I've had good luck asking for concessions, it helps if you point out the comparable rents in the area and note the difference in properties' maintenance. 

Market assessment and evaluation Research into the local demographics and comparable properties in the area needs to be done.

Knowing the market won't be this high for long and that I'm possibly overpaying for a townhome compared to what the usual price would be at this moment in time without the Real Estate boom, I'm nervous about putting in an offer for the long run.

I did a small renovation to the downstairs kitchen/bath and rented it out for much lower rent compared to similar rentals.

If I was to make an offer and I have researched the comparable home values, do I offer the amount then that makes sense to me according to the calculations i.e. have around 8% COCR?

I recently sold our first property because the market was not going to appreciate compared to the market we are currently stationed in.

There are few areas around Orlando where the prices are relatively low compared to the Tampa market.  

But this kind of gets at my main distinction in the question compared to other posts I've read here about the topic...

We don’t know any PMCs to recommend in the Central Jersey area, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

I need to find a way to compare the index funds route to the DST route side by side over 20 years or so.