With the right underwriter you can get pricing much closer to that $150k price with a $482 limit.But my first step would be to find a competing bank that has more favorable, to you, terms.

If majority condo owners vote in favor of the reassessment, then each owner will be forced to pay 50k to improve the building and its amenities such as the lobby, gym, pool, walkways, etc.

Again, if your impatient (Like me) you can find local credit unions that don't have seasoning periods, check out podcast 197 to get your creative mind flowing:)Or you can decide to go commercial but you won't find the terms as favorable as conventional. 

He suggests that I take over the property, do the necessary repairs, fill the vacant apartment....and THEN after the property is in a more favorably condition finally go through with the mortgage process. 

You can do that, but you better have a pretty damn good system to make it work in your favor. 

If I can return the favor any on related HVAC or maintenance questions I will.

On one hand you might be doing them a favor by urging this couple to confront her declining health and consider an assisted living arrangement or possibly moving closer to a supporting family (maybe the kids?).

I keep feeling like maybe I should just save up some more capital to get a more favorable position in a deal.

Your Rochester market is great to cash flow, but as you stated, long term demographic trends are not favorable.

Short to say, that rental income from a primary residence is counted less favorably or more conservatively.Hope that helps, let me know if you have any questions.