Private Money is technically cash - having a contingency definitely protects your real estate investment; I've seen plenty of inspections that have unveiled major property issues that the realtor and or seller did not disclose and were ultimately deal breakers and costing investor a loss vs a gain. 

So, we had an electrician come over and to our surprise, due to a dedicated circuit that was installed for the air conditioner unit (needs repaired, but circuit is fine), the process of wiring/installing electric baseboard heaters is fairly cheap and easy to do.Having said that, I am racking my brain for possible pros and cons of adding these heat sources and being able to call these "bedrooms".

Deal breaker for me.

Probably not a deal breaker if you don't replace it, but that's just my two cents. 

Ultimately it’s not a deal breaker, just a perk that I would jump at if I saw it.

Add in steep hoa and possible hoa restrictions. for those who have made investments in either location, what do I need to consider besides profitability that may be a deal breaker?

I'm looking into building a new multifamily building with separate garages (and electric meters) per unit and the idea dawned on me that while doing it, running 220v to each garage stall might be smart in the event a tenant wanted to charge an electric car as it seems like it would mostly just cost the circuit breaker, wire, outlet and a little bit of extra time.

Trying to buy my first place & preferably a multi family home, but that's not a deal breaker.

These were sold by "National Home" and that may have been located in Tennessee.We always ripped out the 60 amp fuse box / electrical service and upgraded to a 40 space 200 Amp circuit breaker system.

This rent drop makes the OP's situation different from usual, holding out for the previous rent in a depressed rent economy may be unrealistic, and trying to extract it from the lease breaker may also be unrealistic in the current situation.