In late December, at 35 years old I came into a very nice sized windfall in the form of company stock options.

I hope to possibly pull from you and others a portion of your wisdom.

One possible avenue:- You say that this money is only a small portion. 

'Front-End Ratio'A ratio that indicates what portion of an individual's income is used to make mortgage payments.

The listing agent has the responsibility of showing all the offers to the seller regardless of the size of your offer. 

I could go on.Case in point -- there's a LOVELY house in my area, on the water, good size, 1/2 acre backyard, great school, amazing neighborhood -- the house has everything going for it.

Rehab came out to be 33k due to the size (1700 sq ft. with 3 bathrooms) and a decent amount of drywall work.

I plan on taking a small portion of my profits and doing something special to reward my wife and myself.  

Also, you will have to file 990-T every year that you are collecting rent on the portion of rent after expenses attributed to the debt...look up UDFI but you need a tax guy for that as there is a formula.

I personally don't think there's a good one-size-fits-all answer for that (I think few here would claim there is).