From my observations most investors are better off going through a more natural progression of growth.

A more recent one is asking if I want to buy on the East Coast...no again.

You likely want someone with different or even opposite skills and strengths as yourself to have a more balanced approach.

., BRRRR) in most areas to make things work (and ultimately to get the best return); my hope was to find some more "turn key" properties to get my feet wet, but I'll see what's out there and maybe start with a more manageable rehab / lower price point to mitigate the risk of botching the work.

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.2.

Keeping the cashflow seems like a more fair proposition for me and for the investor.I have more to consider, but your post was very helpful, so thank you!

I think I would work towards positioning him to be successful in a typical job, build savings, and position him to be able to do a more traditional purchase.  

There are many services out there offering similar capabilities, often at a more reasonable cost and with a customer service team that values and respects its clients.

We have purchased a few properties over the last couple years paying cash but now trying to have a more concise plan moving forward since finding BP.

Throw in a dose of imposter syndrome and fatalism and you have a recipe for some mood swings right before a property is booked again.From a practical point, I would recommend great photos, a clearly defined target to whom you are advertising and understanding the best pricing of an area really well to ake sure you get booked in a timely fashion.From a more meta perspective, be aware that these listings don't typically get booked well in advance (families displaced by flood or fire, traveling nurses who need a new contract ASAP, and construction projects that realize they need a speciality engineer on-site RIGHT NOW don't book ahead).