With a property manager, you often lose access to the short-term rental tax loophole, which is one of the major perks of STRs.

I do not think Buildium sync with QB.As for the OP—you run the PM so you have full access to Buildium?

It is expensive to get into and my guess is Orlando will be a cheaper and more accessible market for STRs. 

Any advice on preferred property layouts or amenities that perform best in this sub-market (for example, decks, hot tub, lake view, or easy winter access)?

When more and more information is going to go public and can be accessed by the average Joe online, I think RE agents will not fully be replaced in the next 10 years, but the number will go down or remain the same while we have population growth.

Fees to join your local board, MLS(S) so that you have access to listings, key access, E & O insurance, and there could be more depending on your local requirements. 

Pro gives you unlimited calculator access and additional resources to help you make confident, informed decisions.If you’re thinking about upgrading, reach out to me—I can share a discount code and help you decide if Pro is the right fit for your goals.

We’d like to keep the property as a rental, but access approximately $650,000 in equity to reinvest in other properties or securities.Would it make sense to transfer the property into our real estate business’s LLC?

@Damon Silver There is a program that many accounting firms have access to that goes through a questionnaire and then develops the CS study for you.

(in my area the soil of each proposed lot has to pass a perc test if the properties will be on septic or be able to connect to the city sewer if not... you'll need both legal access and physical access... the lot will need to be level enough to build on, etc. there is a lot more to look into but those are the big ones).