And characteristics or traits do you think an “investor-friendly agent” should possess? 

.: Subject To and Wraps are very similar and yet, very different.Subject To & Wraps share these characteristics You are taking over payment of the mortgage and transferring the property into your name You become the owner The loan does not get paid off The lender can and sometimes will call the Due on Sale You have to have money or credit to solve a Due on Sale call They are used when someone doesn’t have much equity and doesn’t want to pay a real estate agent They are used when the seller wants to sell fast They are used when the property isn’t really a good candidate for the MLS because of the condition of the property They are used when It’s a unique property and it’s hard to find comps They are used when it’s a distressed situation that needs to be resolved They are used when the monthly payment is below market rate (that means it cash flows) They are used when the seller wants to avoid the hassles of listingSubject To & Wraps Differences In a Subject To, NO new mortgage is created.

Way too much gambling/luck aspect to it and even when you win for the year the tax rate is awful compared to long term gains. 

Would you consider a Management Agreement with these characteristics to be a red flag?

Personally, I would start by diving into recently sold (6months) properties within a mile that share similar characteristics to your home.

If I wanted to do high stakes gambling I would go to Vegas and get free drinks not pay so gurus to blow smoke.

There are more characteristics though.

I told him I'd gamble that there's no one who even knows that restriction exists to enforce even if an heir lived in the area...the way to legally eliminate them is either get the beneficiary to record a new document (possibly a QC deed) to eliminate their restrictions, or pursue a Quiet Title if you think the person is no longer around or their heirs are not identifiable. 

Let's assume the property has $313,000 in NOIValued at 6.26 M 5% cap loan $4,695,000P+I annual= $413,400> NOI5.216M 6% cap loan $3,912,000P+I annual= 344,460 > NOI4.47M 7% cap loan $3,352,500P+I annual= $294,708 <NOI cash flow + Are you a gambling man? 

4 doors if managed right can make you, $350,000 over 2-4 years. 2 doors  maybe  $200,000 in 2-3 years.Little gamble.