My take on this is, if it looks terrible it's probably hurting you to leave it like that from a "marketability" standpoint. 

I get a decent a mount of off market multi family deals perfect for those looking to house hack in NJ but they tend to be much higher price point

I think the #1 most ridiculous poster is the person living in a desirable, high-appreciation location who has plenty of capital to deploy who asks which crappy undesirable market thousands of miles from where they live is the best place to buy their first investment property.

HELOC are generally balance sheet meaning the loan is held on the lender's book, not sold into the secondary market.

., how well will the market be when you sell the property, and 2) capital expenditures, i.e., can you financially efficiently improve the asset to the end users (renters or users).

If you look at other threads on the Chicago market this topic comes up a lot! 

I don't know if there is an "ideal real estate market" these days.

I am super comfortable on the engineering side but a good civil is great advice.I received a response from one of my design/build GCs yesterday. 

More of a cash flow than appreciation market?

I'm a bit confused on how a good listing broker could net me more when I'm already at the top of the market.