@Sam GuptaRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.So, when investing in areas they don’t really know, investors should research the different property Class submarkets.

They go to apply for a home to live in an find out they can't qualify. 

The same can apply to the $150k properties, but I am assuming they will be easier to rent due to the lower cost.

To apply rent control on a SFH that just became MF discourages this addition and the SFH was not MF for 15 years.  

Opposite applies if the place was listed 6 months before going contingent and then went contingent and so on..

How can I best apply my expertise?

Pretty sure the nonconforming/illegal basement unit issue doesn't apply to owner-occupants of the basement, only if you try to put tenant in it.

Then you will have the time to apply elsewhere for a home equity loan to pay it off early if you are interested in a longer term or lower interest rate. 

@Aubrey Ford If the Zoning permit for the basement unit was never pulled you can either just apply for it yourself or hire someone to apply for it for you.

He had just applied to the local police department.I had another tenant discharge a firearm in an upstairs apartment.