The area is growing and there is new job growth, but the market valuations are starting to feel similar to 2008 when the prices fell by 40%.   

It should be someone who is fine with a small job if I go ahead with just the one window right now.While I'm at it, I might as well ask if there are any maintenance companies you recommend.

I'll do my best to keep it concise and interesting :)About me: - Interest in real estate started while in college (Rich Dad Poor Dad)- Worked in sales and management after graduating- Built a real estate investment portfolio part time while working full time- Quit my W-2 job after 3 years and went full time self employed- Started and sold a successful ECommerce business (Still partial ownership, but silent partner.  4-hour work week anyone?

I agree with some of your concerns, but if you structure your lease term from August-June, you could mitigate the vacancy and still receive rent for 11/12 months, with one month to turnover the rental and complete any improvements that are needed.

When acquiring these old gems, or objective is to improve their energy efficiency by a minimum of 50% (40% on newer, post War houses) while updating the building to provide modern, healthy living spaces for our tenants.  

IF the occupant is financially strong, you use an LMLO,  the price is market and DTI works out and you do a good job of creating a fat folder.  

Your sales skills will be a huge asset, and the money from your sales job will be a huge asset.

Now, if a life event happened you could move out - such as a new job, or getting married and having plans to have kids and needing more space. 

If they won't allow any inspection or previewing then expect a complete gut job and bid on what you can see.Fannie "sent" the property back to the originating bank most likely, banks don't just buy properties. 

I will still be working a W2 job as well.