I have heard that paying off your rental is not necessarily the best choice because of the deductions it allows for, but given the type of loan this house is mortgaged with, is it even possible to buy another home together and start renting this one out when I have a FHA loan on this one?

If it is a one off event I personally wouldn't do anything.

Novice here, I've been looking into off-market deals but don't feel comfortable moving forward by myself.

@Charles PerkinsI am a fan of the slow and steady systematic step by step path to investing success.Many of the gurus say Go Big or Go Home.I say if you are a beginner skier - do you go to the top of the mountain and jump off a cliff going down a black double diamond slope?

Lastly, get off of BP for some of those references.

Your off market deals and wholesalers are on there.

We planned to have it paid off in a year and a half.

Avoid third-party hand-offs.  

HI Joseph,You can always start off by house hacking meaning you live in one UNIT or ROOM and renting out the other vacant units/rooms to offset your monthly mortgage payment.There are several ways to run and make sure you are maximizing your rental income while keeping your living expense as low as possible.

However, these brackets are frequently pulled off by guests, leading to high maintenance costs.