And it's super cheap to advertise there (you pay a listing fee rather than a cut of each booking.)

If i can write off property management fees as an expense, can I pay myself (either as a sole proprietor or LLC) then write that off as an expense as well?

Enforce the late fees every time to incentivize on time payments.

Most of them are however I am "thinking" I may have a shot a negotiating additional money off if I can say to builder that I know they are not paying the realtor fee.  

Basically sounds like you’re putting down an extra $20k for…Him choosing the property (I assume/hope it’s really you both choose or it’s actually to his advantage to pick it, so this I feel can be disregarded.)Him running all the property management. 1) feels like he might get sick of doing all the work and forget why he’s doing it. 2) you’re paying $20k more to not have to do it so how long would it take for property management fees to reach $40k?

You've got to be transparent that you're helping them get a cash offer on their property by bringing them (the seller) together with the buyer for a fee.2.

The fees range from 2-3 points with some type of admin fee in the $1000 - $3000 range.

We have  found a great property management company that is well worth the 8% fee & is responsive to both us & tenants needs.   

I understand there is a 15k initiation fee and $200 monthly.

Generally, when a debtor files for bankruptcy the automatic stay goes into effect, which is an injunction that enjoins pretty much every type of collection activity (look up that code section and read through the subsections).As a landlord, you even contacting the debtor-tenant with a bill or amount due or otherwise could easily be viewed as a violation of the automatic stay, which could expose you to liability (attorney fees, actual damages, punitive damages, emotional damages).