In addition to accumulating deferred capital expenditures you also have the issue of depreciation recapture so that you could end up with a taxable gain on sale of a thoroughly deteriorated property. 

This first meeting will be an introduction/get-to-know-you along with a presentation and Q&A portion.

Any place to find spots to talk and present ?

I have only reached out to 2 local lenders so far (no big banks or online lenders yet) how can or how should I present the option you mentioned to my lender to see if he can do the same for us?

WITH that skill, well it will be obvious a PM has that skill set because they will never present you a problem without also having solutions or suggested solutions right along with it, because they don't fear the conflict and solve problems almost compulsively.  

“The Tax Code isn't out to get you—it actually presents opportunities to reduce our taxable income.” - Steven LibmanThe Tax Benefits You Need to Know AboutJordan has been a tax partner at a CPA firm that’s been around for 25 years.

The major problem with the inventory in the downtown areas is still the massive amount of deferred maintenance. 

You'll lose the benefit on the next sale so deferring the tax for just a few months doesn't seem worth the effort. 

And to me, when an someone with experience tries to win you over with the laundry list of accomplishments in the past, I question whether or not their focus is in the goals of the future or the glory of the past.So if you if present the possibilities of doing deals with you and investing in real estate, you have presented your pitch in a way that creates a better foundation for landing that partnership. 

You may have to wait a month or two for a decent tenant to present themselves anyways so why not lock a good one up early and take only a one month hit?