Ill try to tackle your questions in order...
I have been putting some thought into buying cars that need a touch of work and flipping them for a bit of extra income. What things do i need to take into consideration in order to do this right?
Don't think that extra income is going to be huge dollars but, they can be extra dollars. Other savings can come if they provide cheap transportation for yourself in the short run. I have been flipping salvage cars for the past couple of years. I have a genuine transportation business so some of the cars stay in my business fleet, other I keep for myself in either the short run or long run. Then, there are some they I buy just for the flip. However, I don't buy anything I would be willing to just keep if I had to.
I do have a few questions i have thought about.
Is there any legal way to lessen the hit from taxes? Each car i buy would be hit with sales tax and then again when i sell it as income tax right?
I do rightfully pay the state sales tax when I buy them (Ohio). Considering that I buy mine from a genuine business who follows the rules, there is no way for me around the paying of the sales tax on the purchase price. For me, this is 6.75% so I have to factor that into my calculations when I decide how much I would be willing to pay for a car.
As for income tax, Ohio seems to allow a certain amount of "private sales" before they want to regulate. By staying under that it seems that no one comes after you for taxes. Also, remember that it is sales on the profit. That profit would seem to come for the sale price you put on the title at sale. That sale price on the title is also what the buyer then pays for sales tax to buy the car. It would then seem that there is an incentive for the price written when I sell should be just about the same price as when I bought the car.
Is there a way for me to let people test drive it without registration? I wouldn't want to pay for a full year of registration just to sell the car within a few weeks. Could a dealer license help with that?
Plates in Ohio are cheap at $50 per year. When I buy a car I have 30 days to transfer the valid plate from car#1 to car #2. That gets me 29 day. After that it is $17 to officially transfer the plate to car #2. Over the course of 12 months I have transferred one plate to a couple of cars and If I have had a car less than 30 days then the formal-ness (read: dollars) of the transfer never needed to happen. Of course, this all varied by state.
Yes, I insure them. I have a real insurance agent and I just email over her the VIN when I buy. Liability only on crappy cars with a multi car discount is very cheap here in my rural community. Of course, this varies by state also. An '07 Ford Focus might cost me $115 for 6 months or a net of less than $20 for each month I have it.
Any catches that i am probably overlooking that might make this idea not feasible?
ITS ALL A CATCH. Further more, it is just a legal form of gambling so ask yourself when buying, "how much can I stand to loose?" There might be profits...might. I've done okay but my bigger wins have been cars where I added 25,000 miles on them in a year and then sold them for more or even to what I paid for them with all repairs a year later. Detailed examples: Ford Focus and Toyota Avalon. Those links should take you to more purchases also.
Further advice: it is all about buying the car low enough. If you can not buy it low enough then you will only be able to recoup from selling for high enough. You might have to wait to buy low enough but that waiting doesn't really cost you money. When you are waiting to sell for high enough, every day costs you money carrying that car.
Another wisdom learned is that simple, normal, plain cars sold to simple, normal, plain people sell a lot easier and can bring easier money than unique, odd, special cars sold to unique, odd special people.
In summary... give one a try. You'll learn a lot on that first one!