Plan is to wall it off and convert to a 4br/2ba,  update existing bath and kitchen, new floors,  interior and exterior  paint.

If you are doing your part and really looking at the property and dug in deep on the underwriting, you should be good to go.

For those who have been investing in rental properties, what are the biggest financing challenges you've encountered, and how did you overcome them?

I would think they would.I was just thinking after seeing someone one the news who had their life savings in Florida STR's.I think it is important to diversity and not have all income producing properties in one place especially when it is prone to a certain type of potential destructive weather. 

Hi Kristi,If you plan to hold the property for the next 5 years, opting for a 5 year prepayment penalty makes sense, as it will significantly lower the rate.

First, short term, I'd like to expand my portfolio of just one property into 2 by househacking by owner occupying a multi property.

These are often properties that aren’t even listed for sale.

I can no longer contribute to a ROTH IRA and am looking for ways to accumulate more liquidity long-term to continue purchasing rental properties.

My goal for right now is to gain some funds through wholesaling properties and then eventually obtaining a couple rentals in the next few years.

Should I consider refinancing one or both properties?