He declined unless we wanted a steep discount and then gifted them so funds back to save them taxes.  

For instance, I had a family friend that gifted their home then had a sudden illness that required long term nursing home care.

Roof size approx 2700sq feet- gaf woodland lifetime designer shingles (gives the slate look similar to what's on the house) - If I choose plain architectural shingles, I'll save 2k- TPO PVC flat roof over 10x30 extension- soffit & fascia repair and replace where necessary (some of the soffit wood has gotten rotten and would need to be replaced)- chose copper valley instead of aluminum (said I'll save $500 if going with aluminium)- plywood mostly in very good condition because of great original quality of the wood (said I'll probably only need 3 sheets replaced)- replace downspouts where necessary, maybe he'll replace 1-2- install cobra ridge vent

People who are getting FHA loans on 100k houses are usually only putting down $3500 - and often times a portion of that is gifted, so your option fee might be a challenge for many of your potential buyers.

That is a great thing.I never used Venmo until I had to- someone sent my child a birthday gift- and when I logged in to collect I saw what others have raved about- easy, free and quick. 

I always suggest to my investors send a welcome packet and/or gift to new tenants once they close on the property.

The difference of fair market value versus what you pay would likely be considered a gift to you, which may require the filing of a gift tax return, and would eat into their lifetime exclusion depending on the amount of the gift. 

After closing I sent them a thank you card with a gift card and one of my business cards.

I personally do not give money to family or friends unless I'm prepared to make it a gift.

If all their money was gifted by a relative last week, I wouldn't feel safe doing the loan, if it were me.Are you putting the borrower on a draw system, or are you giving them 100% of the loan up front?