I also agree with Rachel, as working alongside a broker or an individual with knowledge of your area in question would greatly reduce the time spent driving.

I work along-side real estate accountants and business advisors that understand that automation is shifting the accounting industry and it's not as bad as it sounds.

Delayed financing would have you pay in cash, but then come alongside after that transaction and reimburse you the amount (~80% or whatever the LTV of purchase was) and recoup that liquidity shortly after close.The biggest issue with doing that is tying up liquidity.

In all other situations, like the one you are mentioning, I believe alongside many others that it's a huge mistake to make a decision based on taxation.I'm taking an example that isn't real estate because it illustrates this point in such an obvious manner.

Find some local meet-ups and find investors who already have a portfolio and ask what they do to analyze deals and see if you could potentially help them and/or work alongside them as they are researching so you can continue to expand your knowledge. 

The idea is to rent amenities as add-ons for guests to book alongside their booking of your property.

If I were you, however, I would make an effort to work alongside someone with experience in the area of your long term goals (i.e. flipping, multi-families, single family rentals, commercial, etc.).

Real estate can be a very passive investment so you can do it along side any day job, sounds like your will be very involved. 

In my company one of the services we provide is SMS marketing management alongside Facebook ads.

@Jack Hamm I owned B&Bs for 25 years and house hacked living right alongside my guests the whole time and since then house hack a duplex.