House hacking is such a great strategy for a first property—I've seen family members use it successfully and build wealth in the process.

I live in the Portland, Maine area and am currently launching my real estate wholesaling business as a short term strategy in order to build knowledge, capital, and a network so that I can eventually start investing in my own projects such as fix and flips, and both short and long term rentals.

It would still appreciate overtime and build equity all while someone else is paying the mortgage.

I help investors analyze, acquire and rehab (established, reliable contractors).

Go to the build your team tab and find one here on BP! 

There's not much room in the yard to build an ADU so I'm unlikely to do that. 

Building positive relationships with the staff can help facilitate the process and may lead to a quicker approval.Consider obtaining signatures for notification from neighbors in person rather than sending certified mail.

Older buildings likely have nothing but one layer of sheet rock between the floor boards/joists and lower level units.

OOrlando is really well build to operate STR in due to the theme parks and the shear number of visitors we have each year, bu there are nuances to operating a successful one and the learning curve can be steep, but rewards can also be lucrative if you are a good operator. 

I plan to one day aquire apartment buildings for rental income.