I spent 14 years as a CFO/CPA for a $300 million farmland management and equipment auction company in North Dakota. Last year I left it all and purchased a boutique STR company in Arizona. It has been quite a journey ...

I have an opportunity to purchase an off market deal on a property in MD. 

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

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.

We have stared the project about a month ago, completely new interior including adding new HVAC all new electrical, flooring, cabinets, tops and so on along with new driveway exterior paint and some siding.My contractor is also an investor, so we were lucky there, good insight to share and also, he has lots of leads for renters.But he is NOT a good photographer LOL. here are some progress pictures .Also, I will like to share that we are closing on one more single-family property early next week and we have a duplex under contract._________________________________________________________________________________________________________________________________________10/12/2024.

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. 

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

To illustrate:You inherit a property today that your relative/friend bought 10 years ago for 100k.

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?