The faster you learn, the faster you'll grow.Also, Drive through Baltimore and get to know the streets as it certainly is "block by block"Let me know how I can helpNathanael

Home prices are climbing at a faster rate than local income levels; thus requiring locals to rent.Here is my delima:We want to eventually keep our current home as a rental, and buy another house for our family elsewhere.

I think they're throwing their weight around to see what they can get out of you.

Generally, most of the weight is placed on the income and sales comps approaches to determine the value.

Can I use leverage of cashing him out faster(by Dec 2019)?

Is it worthwhile to house-hack a 3-4 bed SFH if it means I'll get my foot in the door with REI faster (assuming the numbers make sense) or is it beneficial to be patient and wait for a MFH that matches my criteria? 

Once you build a model you like that uses sources you trust and appears to align with reality maintaining it is simple.Also, if it really does match the observed reality (or comes close) you can use it to predict, at least generally, enough to include the data at some weight in your decisions, which van increase your confidence.And i promise this is the last word from me - historical (even 2 months ago) data is pretty available since few care after the sale what it sold for.

Appraisal is also not a good determining factor in valuing the property since its not exposed to the market, so dont put too much weight in it.

A cash-flowing property might sell faster than one with cash flow potential but no tenants.My $0.02 ... 

The tenant will pay the service charge which is typically 2.50-3.50% depending.In fact, the nice part about tenants paying by card is the faster payout.