I have not been able to negotiate out the restriction even on their older inventory. 

The gentleman I spoke to stated they have no lender's fees or points.  

Overall rent seems to be higher than east sides such as Riverside, but houses are relatively older as well, esp in the historic district where the city does not fancy investors come in and tear down the OG look of the area.

It's either pay more than the guy who is willing to overpay or just miss the deal.Any feedback from seasoned investors who have been doing this a long time would be much appreciated.

Older properties need more $$$.  

Fill up costs for 275 gallon tank that is 1/4 full still means you put in about 200 gallons or more; when prices crept to $4 per gallon, that's an $800 fill up that lots of tenants won't be able to cough up, or if they do the rent might be short ;) And it will need to be filled multiple times during a normal heating season; this past December, being so warm, obviously reduces that a bit this season. 

If you want a tie-breaker,  you can hire a structural engineer for around $400 - they will give you a clear statement as to what is needed.Also, be sure to consider the age of the house and where you are lifting e.g. near a bath, kitchen or other potential drain line) - if it is an older house and has cast iron pipes, you will probably have some plumbing work when you are done lifting. 

@Michael Kennedy if you are talking about homes that have been converted to multi-family spaces, I would say either the Highlands or Old Louisville...those spaces have larger older homes that in many cases were converted to have multiple living spaces inside.

Also, some condo-tels will take the profit from all the units combined, and split it up and distribute it to the unit owners at the end of the season.  

Not all lenders track guideline changes.Most lenders base their knowledge around water cooler chit-chat, which is disappointing but true.Classic Example: The Americans with Disabilities Act, and presumably the corresponding mortgage guideline changes, was like 25 freaking years ago, but I still had an older coworker shocked and assume fraud when I did a loan for a guy on temporary disability.