I would stay away at all costs. 

if he's getting into capital raising to raise 25k or 100k he needs to stay with his corporate job. raise that number by 10x and do something that's life changing. challenge yourself. 

- Any tips for staying updated on regulation changes?

BOI is paused again, different 5th Circuit appeal struck down the stay

Florida should be busy currently with people staying in the Winter to get away from the cold & snow. 

Stay curious, keep learning, and you’ll build momentum in no time.

You could live in one unit and rent out the others to offset your mortgage, staying within your $4,500/month affordability limit.

I see 3-5 as a fad.Fractional ownership - way to much overhead for these to be profitable. think "timeshare".STR in non traditional markets - running a STR is a business and real estate, boils down to location location location - who would want to go to a conference and stay in a STR vs. the hotel where the conference is at, most businesses pay for this I do not see why.Mixed use with green - this has been going on for years- it will continue but it is also more expensive to build - which means higher costs to use.Not trying to be debbie downer, I have seen these attempted to be done in the past and they really have not been successful.I do really like the BTR model though as I continue to see that as a very good option in the future. 

Even if you have a good framework, it's much harder to manage virtually and stay on track.

You need to know how to analyze property and then systematically evaluate property on a daily or weekly basis to stay on top of the market.