One has a little bit of a steep driveway, but not too bad.

It is possible that it will comp out but I might hire an appraiser to see what they come up with.It depends on how bad you want it.

Maybe not as bad if not in a beach town?

Used PSI last year, they did a bad job, the snow wasn't even bad last year and with several attempts asking them to do better within the terms of the contract, they still sucked. 

Quote from @Chan Park: The first leak was allegedly due to bad caulk.

And end of year actuals never pencil out like the spreadsheet...I'm not saying that it's a bad idea; I would just urge you to proceed with extreme caution.

Now to the bad news: it is REALLY hard to be a 20yo real estate agent and make a living wage, let alone generate cash for a down payment.

There are two reasons this is a bad idea.Investing with an SDIRA (assuming it is not a Roth) will often result in paying significantly more taxes. 

I’ll be honest it’s not clear to me real estate is necessarily a better investment than say the stock market, certainly not a bad investment but not as hyped as some people make it, you need to decide how much owning your own home is worth to you & also how long you plan to be in the area, if you will be here for the foreseeable future, bite the bullet and buy, if your not sure where you will be in a few years, renting might make more sense.

It includes a lot of good/bad examples.