As a young professional I stick out like a sore thumb on this street; however, it doesn't bother me because I'm here for a reason. 

Have you gotten particular favorable treatment through them in the past that you could share?

Also, a suggestion for siding treatment and color:https://i.pinimg.com/736x/d1/65/06/d16506fe56a57f8f6a50276ce7303e2d--exterior-windows-exterior-colors.jpg Cross-gabled windows (visualize minus all the Tudor half-timbering):http://idolza.com/a/f/e/english-tudor-exterior-paint-colors-and-on-pinterest_tudor-style-windows_hobbit-house-designs-how-to-design-a-bedroom-small-bathrooms-mens-ideas-best-countertop-material-open-liv.jpg This could look outstanding, and bring it all together... look at the curved gable on the upper far right of this house.

I plan to work until retirement (hopefully less than 4o hours/wk), so RE is to supplement my income and my other retirement.

No special treatment for seller credits on investments, standard rules apply.

If it is a lease you are required to demonstrate that they are no longer meeting the lease requirements, so re-read your lease.  

It is never going to be the right time, you will be tired, sore, and even miserable at times. 

Then the lender's only apply x% of the 1099s.Wife's firm W2 helps, but using combined income still requires the SE treatment.

I am not familiar with the system you describe but can give you a reference for a good well/water treatment company in your area if you send me a private message.

Seems like a really good way to get ideas for more elaborate projects.With this one I'm looking more for simple suggestions of what treatment may look good with this type of building, even from people with no design experience.