Dusty,
You are getting a good variety of responses here. It will be interesting to see how the opinions play out as more members chime in,
I am in 'somewhat' of a similar situation. First let me say my initial reaction to your title of the post was 'that seems like a weird way of doing it'..... but take that with a grain of salt - I am only one property into what I hope is the first of several if not many more properties. It seemed a bit 'impersonal' to me. I like what the others said about calling and just getting together for a chat/coffee etc.... But I may be way off there!
My current property is a Buy & Hold duplex, that I bought in a 3 way LLC within my SDIRA. I plan for future ones to be both within and outside of my SDIRA. Not sure if you are familiar with the lending rules for IRAs, but it is VERY hard to find loans for properties held within them as the loans MUST be 'non-recourse'. Only a handful of lenders do them, or Private Lenders can also. On the ones outside of the SDIRA I assume I will run into the whole issue of showing a 'rental history' of one to two years etc and would be looking for a 'starter loan' until the time I could refinance into conventional products for the long term.
Overall, I would be looking for terms of 3-15 years on these loans. My plan that I am JUST starting on for seeking lenders is this: I made a list of about 150 people who I thought had 'potential' as my type of lender - some are family, friends, neighbors, business associates, civic club colleagues, and a BIG share of them are past customers of my Contracting Business that has a 25+ year excellent reputation and many customers I have become close with over the years.
I am working on putting together some 'sample' packages showing the type of properties I would target, explaining why I am seeking Private Funds, how the loans would be secured, etc.... I have talked to the first couple of people, who know I have one property and am looking for more, VERY casually explaining that I would just like to use them as a 'sounding board' to bounce some ideas off of how I would like to seek these funds. I am asking them for feedback good AND bad of my thoughts, plans etc... ; what is appealing, what would make them nervous etc.....
I know some people on here seek 'active' private lenders who are 'seeking' our borrowers and are obviously very comfortable doing this. My plan is to offer an 'alternative' to 'casual investors'; those who have either large retirement funds with sizable portion of their funds in low yield instruments like CDs etc or other liquid cash in large amounts (sold the farm or business etc..) and might be interested in getting higher yields all while helping to improve their local communities.
I too am from a smaller town....about 10,000, but our school district is about 25,000, country about 70,000. A large part of my previous customer base is from about a 4 hour drive radius from here....Chicago, Minneapolis, Milwaukee, etc who have vacation homes in my area. If they have vacation homes of 300K - 1M, they likely have decent retirement funds too :).
Just a bit of a ramble, but I think the more we all share the better for all of us!
Dan Dietz