Meeting them face-to-face goes a long way in establishing trust and credibility.As you engage with investors, it's essential to build and nurture your investor list.

It is best to establish a 3rd party servicing company to oversee these payments as you do not want to send this money directly to the seller as they may not actually make the payment and then you could see your house foreclosed on by the lender.

Would you mind sharing any advice or experience that you have with paying Property Managers a commission for their workWorking for same brokerage for 5 years as a 1099 Property Manager with established properties..

Communicate, treat everyone with respect, and provide ample time.

I sell real estate to STR investors in a beach market, and one of the main strategies I tell them about (and that I also use myself) is to have a new 4-point inspection and a new wind mitigation report done periodically and to reshop insurance with a few BROKERS.In Florida, these inspections are only good for 1 and 5 years, respectively, so you MUST get new ones--especially if you have had a new roof, added hurricane clips to an existing roof, or replaced your wiring, HVAC, water heater, etc.Also in FL, insurance companies come and go, so there is no need to stick with the same one and just take it when they try to bend you over and raise your rates. 

His story, if true, indicates the tenants have no respect for the property owner, his rights, or his desires.If I were a betting man, I would bet money that they are dragging their feet because their rent is well below market.

Your next contact, is laying the foundation, often detailing the "problem" and establishing as a problem solution provider. 

(a) If the Company establishes the title, or removes the alleged defect, lien orencumbrance, or cures the lack of a right of access to or from the land, or curesthe claim of unmarketability of title, or otherwise establishes the lien of the insuredmortgage, all as insured, in a reasonably diligent manner by any method, includinglitigation and the completion of any appeals therefrom, it shall have fully performedits obligations with respect to that matter and shall not be liable for any loss ordamage caused thereby.. . .To the extent that you are requesting compensation for the Alleged Damages, please see Condition8(a) of the Policy which provides the Company with the right to establish title as insured in areasonably diligent manner without being responsible for any loss or damage to the insured.

Im curious about how the successful private money lenders have established terms that have been win-win for you and your lenders.

You could find a partner to help establish an LLC that rents out your property long term, then subleases on a short term basis (master lease is one that is designed for subleasing, it is a way many people pick up STRs without actually purchasing any property, they just find owners who are okay with them subleasing on a STR basis).