He was happy to allow me to rent out nightly because it actually helps keep his property in better shape than a long term renter (having a cleaner in there every turnover, short stay guests always let you know when something isn't working, etc) but didn't want to hassle with worrying about a percentage of income/management, etc.

Couple is splitting up and one is wanting to stay. 

- Any tips for staying updated on regulation changes?

I currently own a few properties here in Bryan-College Station, I have a full time sales job so try to stay as passive as possible. 

You'll be tagging transactions throughout the year with categories that fit the Schedule E so when tax time comes (if you stay on top of it) every deposit and expenditure will already be categorized and it's quick to create the Schedule E and/or run P&L reports any time you need to.

Payments stay lower, cashflow better and it'll boost your balance sheet not to mention lower risk when things go awry. 

Establish a system to stay in front of potential sellers & buyers.

For example, I have two STR high-income earners (making 140k & 150k) in Joshua Tree for sale with low expenses, where the sellers will stay on to manage it.Making sure you are keeping as much as possible from the tax man is a huge component and to do so you usually have to invest it.

Its a hard explanation on this part of the industry however I have decided to stay away from real estate and continue my path investing in the SMP500.

Solution: You are not going to like what I am going to say here, but it really comes down to your self-discipline, which is why this is probably the hardest aspect of achieving your goals.