It's a big job, 1400 sqft of deck, several different levels.

You're on the right track being on here though the more you post the faster you learn. 

Generally, styles tend to change faster than cabinetry gets too beat up to use.  

I am looking at taking it to the next level and have been toying around with the idea of some 4 unit apartments.

I have worked with Four Seasons on many jobs and know they are very good.I don't know all of the specifics for your house or experience level, if you are planning on fixing yourselves or through contractors.

It would be interesting to see this chart on the zip code level.

Historic levels average around 3% and we've been around 10% for a couple of years and will probably see the same again this year.

So using the same funds it is better to buy 2 entry level homes than one mid level home. 

Selling a high-dollar single family house may be able to get you multiple opportunities in another area and that is how you can build your cash flow faster. 

Its not unheard of for an agent to request the buyer cover the difference between the commission stated in the MLS and what they want to get paid, however in my opinion, only agents or teams who really provide a high level of service deserve to charge extra to a buyer.