There is also an ease of financial management; it's easier to keep business and personal finances separate.

The HOA/by laws will be your first insight into how restrictive these resort style communities are to keep up with the feel and look of the community. 

Then, in two years, you can go out and buy another primary house renting out the entire previous house and keep doing that to build your portfolio.Smart!

This means that, while companies may "require" experience with it, they may not actually be able to find a good candidate who has that experience.

@Logan Rex if you are considering selling the SFR and going with a Highrise for house hacking purposes of eventually after the year or 2 and then keeping it as a rental.

For that, it doesn't mean I wouldn't buy it or make a market for it.

Maybe there's something I'm not seeing, or maybe I just need to keep looking for something better.

I will definitely keep in mind that not all properties will cash flow immediately and to focus on the long-term investment.

**Insurance and Liability**: What insurance considerations should I keep in mind, and what liability clauses are important to include?

They are worried about underwriting the deal to today's costs with the concern that rents might not rise to cover the additional costs (keep in mind, I'm in FL with huge insurance rate jumps...but other areas are feeling similar pain).