For SWFL locals, I would like to discuss your tactics in this current market, where prices are still way up and rates are as well.

ALL,, even parts of East Cleveland, ( I know what you're saying this guy is crazy east clev, well pricing there has double tripled or more and IMO going higher, those in the know understand why ) Parma good luck making money there, you missed that boat by 5 years, even GH prices have tripled or more over the last 5, 6 7 years.

The prices in that pocket have jumped.

(assessed value of the house, or price listed on the ad) x the tax rate of that state! 

It sounds like you need to take a HELOC out for the downpayment though as 30k is not enough for a four fam purchase price in Boston. 

What's a reasonable amount of time for a property management to tour, provide quotes, and get a property advertised for rent after a tenant moves out?

I myself will, IF I am convinced that the property has a specific reason that ensures the likelihood of near future strong price appreciation.  

It has started to slow down slightly with more inventory coming available in my area and now that I’m asking higher prices.

It sounds like the LO and CU you are using likely did not have that option and they said pricing is the same. 

So, updating a 1940s ranch is a perfectly reasonable sounding thing to do.