Been kicking around the idea of buying larger acreages of land and subdividing and selling and/or renting.

The deal referred to above is an 8 plex and would be a perfect stepping stone into larger multi family.Any advice on this topic would be very appreciated. 

Make sure you check out the past projects of any craftsman you are considering.....installing banisters is a really difficult task even for good carpenters.

I've always believed that it's better to work to hit a single than to try to hit a home run in your first deal, in the larger scheme of things.

The issue is larger than STR bans and IMO the right political approach can make a difference. 

The sec121 exclusion is usually one of the larger reasons.Hope this helps. 

We are looking to grow our portfolio in another market, but we are on the fence about hiring a property manager for these properties or just hiring a hybrid type property manager that will just handle leasing/open houses for leasing/small physical tasks (handing a new tenant key, etc.)

Is there a simple but repetitive task that realators wished they had a simple software or app solution to?

His disabilities prohibit him from doing "normal" everyday tasks like answering the phone, speaking to others, and working outdoors. 

I think people will start to reach higher for more house knowing this(probably already have but more will do so) and eventually traditional financial institutions or new FinTech firms will capitalize that short-term rent potential into larger loan eligibility.Things like work from home obviously accelerated the shake-up and gave people an ability to get out of the mega-cities like New York or LA.