(still aren't sure if we'll flip or hold).I am trying to structure an offer that, both, makes our investment worth the return AND isn't offensive to this retired gentleman and his wife. 

If it is not the case, I might hew closer to James' recommendation but with a bit more tact (no offense). 

No offense and I've seen worse but dude the decor is god awful.

. - You're a new lender and don't know what you're doing yet (no offense meant, just pointing it out because this more experienced borrower could potentially take advantage of that)- The information a couple posts above, which you agreed with, about the borrower taking care of having the loan documents prepared is not correct. 

And if you're so worried about renting to recent graduates, have one of their parents with income/good credit co-sign the lease for extra 'insurance'.No offense, but it sounds like you worry too much and are creating hypothetical negative situations in your mind which serves no purpose.

you are absolutely right and sorry if i came off offensive... i am a consumer and have had the same exact experiences. agents who put you on set it and forget it through their portals which will narrow down properties based on area and other general details and never contact you again unless you call them and there are agents who will go look at properties for you because you are stuck at work gather all information and give you advice to continue to examine or list 25 negatives to talk you off your emotional impulse buy. it took a few agents before i found one who doesnt mind to work for their commission and i will use him on every deal within his license jurisdiction.you cant expect a consumer to be happy to work with someone who just goes through the motions because they've been in the RE space for 20 years.. much rather give a recent college grad with some motivation the business.you sound successful and i am willing to bet its not because you set it and forget with you clients and you actually work. god bless

@Justin TahilramaniNo offense taken man.

We knew having 2-years with a family was appealing to a landlord, as we are more likely to take care of the home than a house full of college kids (no offense, college kids).Second, we signed a lease knowing that we were going to rent out the english basement on AirBnB as much as possible (which we had the approval in our lease and from our property manager to do).

However, you probably don't know that the had a lot of complaints against him for saying things that were offensive, political, or otherwise not conducive to the topic at hand.

You definitely sound like a novice, no offense.