There are fees associated with going to Real Estate school, obtaining your license, joining the board and MLS for your area, getting proper E&O insurance and so forth. 

However, I am unsure on how to go about finding the proper handyman/maintenance guy/management team to help run any out-of-state investments I make.

Quote from @Grant Shipman: Hey BiggerPockets Community,If you’re raising capital for real estate syndications, you need to be aware of SEC regulations—because one wrong move could put you in serious legal trouble.Many new syndicators think they can just start pooling money from investors without following the proper rules.

Start by talking to a cross-border CPA and attorney to handle taxes and legal structures properly.

They have a bigger single family home and a tiny home on the property, but there close proximity and shared driveway present functional problems that are undesirable for guests. 

If you are looking for proper guidance from someone that has house hacked quite a few times and has the knowledge and experience to help get you going in the right direction, I recommend reaching out to @Josh Green.

We get inquiries all of the time on Airbnb/VRBO/etc for large group functions at our properties, even if we say in the listing it is not allowed. 

I would generally say no if you don't have a property unless you're looking for peace of mind knowing that you've set your financial life properly. 

The forum will be here (and honestly, I use the Search function a LOT).

Our property was already functioning as a short term rental so it is furnished but they are getting rid of some of our furniture and putting in new furniture and they are just charging me for the removal of my items.