I’d definitely recommend visiting and getting a feel for the areas, although we’ve wholesaled to plenty of buyers who have never made it to town.

Keep up compliance with all legal and regulatory requirements for LLC ownership, such as upholding state law duties, filing yearly reports, and keeping separate financial records.

- You need a laser printer capable of printing legal sized documents and scanning them which can cost upwards of $500 if not more.

So today, when contractors tell me bigger numbers for work that I know l can do it is hard to let it go.It was also a process building a good screening process and staying on top of legal changes that effected leases and other processes.  

Touch Stay is pretty cool, I have no experience with it but it definitely looks cool!

I'm probably just reiterating what's been said above, but definitely house hacking.

House hacking is definitely a great way to learn to be a landlord on training wheels.If you decide to rent to your friends, I'd still treat them like any other tenant.

As stated in the post, I am definitely leaning very heavily to investing in another house hack and building up the equity further for future plans. 

She refuses to do so, bc he has legal issues and want qualify and meet the lease requirements.

While the HOA might tank your profitability, I do know/am frequently messaged about condotels for STR usage, so it's definitely not that uncommon of a strategy.