I've been dealing with an unresponsive property manager who is no longer managing properties and has shut down his company.

The reality is, rising property taxes, maintenance costs, increase insurance premiums (I'm a broker so don't get me started here), an HOA assessment or annual increase, etc, etc, etc.

Sounds like you have a good understanding of the strategy.I normally work with clients by giving them a price range of a property they need to buy to get to their desired tax bracket.Best of luck.

The property's location is ideal for short term rental (Orlando area theme parks and convention centers.)How did you find this deal and how did you negotiate it?

I'm looking at house hacking a duplex or the like for my first investment property and looking for some advise on timing.

I still own the property and it has always been fully rented/

It's been nice to build different plans and seeing how/when the addition of more rental properties plays out in reaching my financial goals.Just wanted to share, thought others here might enjoy it too!

The first property I ever purchased was a section 8 duplex in North Philadelphia.

However, I would suggest you calculate a 5-10 year pro forma on each property and calculate an overall IRR for each so you can compare and contrast based on your risk tolerance.

Happy to chat if you need some guidance into areas and property types.