But here's the bonus - If you convert it to a rental and then sell while you have still lived in it for 2 out of the 5 years prior to sale you'll be able to take advantage of the primary residence tax free exclusion. 

I always give a bonus to my contractor after my closing. 

In these mid-range areas, I like looking for Washington Local schools as a bonus but not to say stay off of anything in Toledo public schools.

If accelerated (bonus) depreciation (cost segregation) is still available, it will be a large amount removed from the prior gain.  

I bought it way under market hence my $70k HELOC when only owning it for a year and a half now.Pros of replacing windows (pretty obvious) - no complaints from tenants on window operation (although this hasn't really been an issue so far w/ my current tenants), bonus in ARV when/if decide to sell, and energy efficiency.Cons - roughly $10k expense, if I use my HELOC then $10k of the balance goes towards a non cash flowing investment (I don't interpret new windows as generating cash flow), if I finance then I add to my DTI which could hurt me when attaining future loans on future rentals.I tried to keep this as concise as possible while laying out the full scenario.

If he added value by saving $2,000 on materials/labor, would he get a "bonus"?

It has 3 bedrooms, 1 bath, formal dining room, full basement, library (probable bedroom #4), very large attic (possible bonus rooms (?)

you get 0.5% bonus on that for dream accounts as I mentioned (but only ever 6 month i think).

Usually the bonus points of a personal card and a business SW card will get you real close to the 125k points. 

Bonus if they're familiar with Baltimore city/county.