I use Appfolio in our business for LTR and we really enjoy it.

We have a normal REI business with this 4-plex on the side and it takes some juggling. 

Yes you can use the cash out proceeds to payoff a mortgage balance for an investment property since it is still qualified as business purpose use. 

LLC's are more used by larger investors and people who do not qualify under their personal names and have to ue business purpose loans and they require the property be in an LLC and not an individual.

As I've been learning, there are the key taxes to understand when investing into a new area or state:- State business income tax (if you have an LLC)- State personal income tax (if they want to tax you too, even as an out-of-state investor)- City personal or business income taxes- Any registration fees due the city/state- City/state property taxesAnd I'm sure more!

I currently have an airbnb in the Tampa Bay area which is performing well.

Appreciation is just the cherry on top.The last few years Toledo somewhat caught up with appreciation but I believe we are capped now.It's a slow moving market and always behind the rest of the country.There is just not enough demand/infrastructure growth like in other markets to support continued appreciation.Historical data shows the Toledo market appreciating at the pace of inflation which is nothing to brag about hehe.IMO, it's a cashflow play and you should consider building a larger portfolio because it will be safer.Owning 1-2 properties can be a "hit and a miss" and really not the providers or PM's fault.There is a high likelihood of turnover so it's important to build a larger portfolio.If you experience "drama" on 1 or 2 properties, the other 4-5 are performing and can subsidize any losses incurred on the few that temporarily aren't performing.Wishing you much success

Then speak with the planner to see what types of businesses / buildings they think are a good fit for the property based on the master plan for the area. 

The condo has to perform in real life.

I've always used my business solely to generate an income/paycheck, however I'm ready to transition and use my experience to facilitate investment opportunities.