Quote from @Joshua Thompson: If it helps, I asked many clients this same thing and learned the clients who spend time each month updating books and records are the ones who spend less than 30 minutes preparing everything for us. 

And you need to keep detailed records of all repairs and improvements.

Accurate records of all expenditures are essential to claim deductions and calculate the cost basis for future capital gains taxes, including depreciation recapture.This post does not create a CPA-Client relationship.

What I've seen is that when asked to provide an assurance that a loan wouldn't be called because of a due on sale clause being triggered, the lender customer service typically just outright says it's not allowed, or default to a "no", because they see it as a black and white question, and miss why the due on sale clause is actually written into the mortgage document to begin with.If one is transferring property title from personal name, a Grant/Warranty Deed would be drafted/recorded to transfer title.

I don't necessarily need the standard features of pm software, such as rent collection, bookkeeping and maintenance requests, though that could help; but do need a clearinghouse of important information, such as leases, legal docs and other information; maintenance vendors I use; maintenance history; and some kind of tracking system, where I can record the various current projects I'm working on within the business.

Make sure to prepare a professional proposal, highlight your STR track record, and be transparent with your financial projections.

Success stories are happening every day,  I have clients breaking record rents on house hack more so than ever.  

I recorded a virtual tour on my cell phone because I was getting tour requests I couldn't fulfill, but no one has asked to see the property since I made the recording.

Account Closed It will only show on your credit report if the person who is holding the notes goes to a servicing company so it is recorded.

However, once you have a relationship built up and solid track record with your private lenders, you should be able to also do 2nd (and even 3rd position).