Hi Mike - I have automated messaging for several points throughout the guest pre arrival and arrival and check out process, however I supplement that with my own messaging such as asking about restaurants or if they want to stay an extra night.

If you have a good paying day job rental homes might just be a supplement to your income.

There are specific requirements for the solo401k.You must be a business owner with no common law employees and earned income to supplement the 401k plan.

thank you for all of the great responses.My original goal was to end up with approximately 10 SFH to supplement my retirement, but now that I have a couple in the works, I'm open minded to all aspects of RE. 

If STR isn't considered a rental activity under IRS code, then how can it go on Schedule E which is for supplemental income from rental income?

I am also trying to collect as much as I can from the sellers but not everyone has great data which is why I'm trying to supplement with an online tool.Where does the data come from when using AirDNA and Awning. 

This is a great way to supplement your retirement income from 401k, pensions, etc. 

I used lending to supplement my Brokerage activity did both at the same time.

I understand that for high-income earners, this is not a big concern because they supplement their primary job.

I think of if I had to buy my first house two years ago when I was just about to get married, having a variable income with no cash flow supplement, it would be a dramatically tougher situation.