I’d be happy to connect you with several seasoned mortgage brokers here in Austin that we work with.

How feasible is this plan from the POV of a seasoned investor?

Establishing relationships with seasoned, established, 'key players' is definitely the first step towards success! 

You need at least 90 days of seasoning for any DSCR lender to use the new appraised value.

Alternatively, if you want to connect I'm also a licensed agent for ERA Live Moore, seasoned investor, and have access to off market listings that might fit the bill for a first multi-family / house hack investment property.

I know very seasoned flippers miscalculate or get cocky because they've done a ton of deals and wind up losing tons of money.I would figure out what you are good at, have a passion for and gets you to your ultimate goal (financial freedom, generational wealth, quitting your W2 etc) and work towards that sooner than later.A good place to start in Orlando would be networking with other investors that are local.

Plan ahead if you buy in a seasonal area.

Owned for over a year but still working on the STR seasoning.

Furthermore, is there a seasoning period required for this if it is a home I intend on occupying?

I’m glad to join this group where I can learn from seasoned investors, and I can help anyone that wants to move or invest in our area.