Fed decision imminent with 98% chance we have a 25bps reduction per CME watch tool. 

Here are two deal diaries of such setups -- one, a young couple who were living there and renting the place by the room, and the other, a young couple who were off-site but still rented by the room.It can certainly be done and is a great way to get your first place, have mortgage reduction (maybe even cash flow), and get some landlord experience.

I recently sold a house and they had a home inspection and they came back with a list and I simply told the buyers , No to any price reduction or the "repairs" .

Using your $100K example, the 6% seller assist is far more valuable to this buyer than merely reducing the purchase price by $6K because the 6% seller assist is a $6,000 reduction in funds required to close whereas reducing the purchase price by $6K equates to less than a $200 savings (2.5% down payment + some incidentals).

There is a lot of weight on marketing, and a lot of inputs to that cycle.

If it is block construction the engineers will make you beef up the slab and add piles to support the new weight of the second floor.

If you are willing to wait we are most likely going to see 100 basis point cut over the next year and a reduction in the spreads that lenders are working off of.

After weighting all of that, does it make the most sense to try to keep this tenant in place? 

This reduction in access is what the compensation was to be for and tenant complaints will be many and with creative language. 

In the limited instances where I do collect a fee on the purchase I often roll it into the deal and take price reduction.