The area I described is older and the houses will be a pain.

So if you just have some random house 10 blocks off the beach that's different than a house that is 2 blocks off the beach with a pool, which is again different than a house that's on the beach. 

It is only a matter of time before they migrate a few blocks south.

Prior to driving around I had been considering houses a few blocks back off the beach, but after going there and wandering the area, I realized for the type of property I was looking for it needed to be on the beach.  

If you can justify your request with sound reasoning such as they are rentals on the same street or within x blocks making it easier for them to manage, I would say go for it.

I do the same but with Quicken that I've used for 30 years even though they've been making it a bigger pain every year.

The house is well maintained but there are always a few things to be done after the green card inspection but this process has been painfully slow (our inspection was Feb 2020 and we still haven't received a report).

Just like most markets it is block to block in regard to B-C type locations.

There are entire blocks in North Lawndale with abandoned "at one time high cap rate" properties.

Which after you have paid for an appraisal and invested a couple of months submitting and chasing down documents can be painful when the UW sends out the suspension or denial.