By turning it into a rental, you may be on the hook for capital gains tax in the future vs using the 250k exemption for single filer or 500k for a married couple that files together on capital gains if you were to sell now. 

I've already done quite a bit of research in my area and can already pretty much tell you what a property is worth or at least generally what it will sell for as I spend about 3 hours a day looking at properties and have been doing that for about a year to make sure I'm prepared on the accuracy side of things.I do have a family member that is a real estate agent in the area, but I'm not sure if a standard single family residential agent is the correct connection for multifamily.

We don't want to sell its been in family for generations. 

Or Sell?

In that case would you sell or cash out refi to use that equity elsewhere?

Hi, My partner and I are in the process of selling a property in Annapolis Maryland.

If you rent by the room, you should be able to save money for the next place or sell it.  

Something you have experience buying and are easy to sell.  

DSCR lenders make their own guidelines that can be similar to conventional loan guidelines but are often different as the DSCR lenders generally sell their loans after closing to replenish their cash to investors who have different guidelines depending on the investor pool. 

Although we are targeting good neighborhoods for appreciation and to make sure we get good tenants who maintains the property well and pay rents on time, having a positive cash flow is an absolutely necessary piece to make sure we make money on the investment from the beginning instead of hoping to make money at the end when we decide to sell it.