I'm currently househacking a duplex and I used an FHA loan, albeit it was a property that was on the market for 3-4 months.Would not suggest sticking with a realtor that pressures you to offer something that you're not comfortable with.

A lot less risk in this strategy and you'll be able to gauge whether it's a good idea or not.

You'll likely find that the time pressure of identifying three addresses in 45 days that you are going to close on is not a given.    

Some of our larger companies will gauge you.

You may want to let the tenant know this in advance to gauge his concern about it.

I know that the purely safe play would be to buy in some out-of-state market, but like I said this is a property in which I have interest and I'm trying to gauge whether it's a reasonable risk to take.So what I want to ask here is: what kind of questions do people here ask themselves when considering deals that have elevated risk like this.

I gauge dropping the price based on showings.

A great lender will walk you through all these options, show you the fees included, and help estimate your mortgage which will help you better gauge your cash on cash return with a good house hack or traditional rental.Good luck!

To get a good gauge on current underwriting parameters call one of the big banks and talk to a loan officer, then call a local credit union and talk to a loan officer.My understanding on a cash out refi is that you need a $50k minimum loan amount, 80% max LTV, and if you purchased in the last 12 months, they will use purchase price for value, NOT a new appraisal.If the home appraises for $65k that's great because that'll put you under 80% LTV.

If you need cash flow NOW vs in the future, the pressure could create great results, or it could cause you to quit the industry before your "pinata" breaks open.