The way around this is if you get a big gift from a relative or anyone wait like more than 90 days or more before you try to get a loan.

You can offer a gift certificate to somewhere cool if they sign lease ASAP.

In the beginning twice a month is probably great, but once a month is probably fine too - most of all it has to be do-able, and if possible automate this if you get too busy.Finally, if you're a perfectionist and find you're getting hung up on over-planning and not executing (this has been my big problem, I'm not saying it's yours :) a book I think is excellent is "Finish: Give Yourself the Gift of Done" by Jon Acuff.Apparently I'm incapable of writing a short post. :)Would love to hear how things work out for you, I know people throw around a lot of dismal stats about starting out in real estate but I was a long shot and I lasted (including through the recession as a single-income person, my husband conveniently showed up in 2012 :) and I have a friend who started out new in 2007, right when we were gearing up for the recession - she did amazingly well while other agents were leaving real estate - combination of good sphere, amazing work ethic, high competence and she's very good at articulating her value. 

No one can predict how far it will fall, time will tellAll to their own,  I prefer to buy in rising markets, easiest way to make money

I plan to continue being the easiest option for when he does finally decide he is ready.

and would there be some gift tax for the person that receives the loan? 

I often find local banks to be the easiest to work with.  

When I turned 18 my father gifted me 14% investment in a condo.

My answer is usually something like this:For someone who was gifted or inherited a small property (or even someone who actively purchased a rental but is not looking to grow the portfolio) the switching cost to a new CPA may not be worth it.

The easiest way is through a sensitivity analysis.