With this strategy, I spend about 5-10 hours per week "managing" this portfolio and it handily pays our families bills. 

It would likely be best to spend a couple of weeks there, if possible, setting up some meetings with property managers, realtors, and contractors.And I strongly suggest you get a property manager at first.

Be carful spending money to fix the repairs up since you will not likely get any more that what his deposit totals.

Would it be better to bite the bullet and spend the $35k (will be using conventional loan)  up front as a down payment and have a home that could potentially be a rental when I move out in 3-4years or rent and pay someone else that $35k in rent over the course of the next few years.

In my research I found that hotels spend an average of 8% on marketing/sales. 

Best case she realizes you're serious and won't spend her rent money on another vacation 

Welcome, BP is worth spending a lot of time browsing.

Replacing kitchen cabinets and counter tops to not only look professional, but to also do so without spending an arm and a leg. 

You can easily spend scores of hours dealing with this issue and may not have any success.It likely affects your property value more than a few hundred dollars.It may result in happier and longer term tenants.The risk is they tell all of their homeless buddies who now set up behind your rental in hopes of getting an easy $100.It is just moving the problem elsewhere but in this case the NIMBY can affect your finances. 

As a buyer, my lender flaked out 2 weeks before the closing date so I scrambled to find another lender.