The meetings have been sporadic lately but are becoming regular again, with the next meeting on the evening of Tuesday, March 10. 

All, of course, being educational in nature and not legal advice! 

Contribute to a regular IRA as non deductible contribution as a backdoor to a ROTH.

If he's not expected to be able to pay much (or regularly), you might find yourself in the latter category.I don't know if you have an accountant now, but you probably do want to at least run it by one.

Natural or LP gas and who is going to pay for the conversion.

Whether something is by the job or by the hour would depend on the nature of the repair.

I am a firm believer that if you are investing in real estate directly, versus a passive model, you need to be doing site visits regularly, and being somewhere you want to go, especially if this is a side hustle, makes it that much easier.I do agree with @Derek Harris that, why not invest in both, if possible. 

Then, after doing some math, I figured out that many of these properties would be extremely difficult to maintain a steady cashflow from and the looming risk of natural disaster was, well, looming.

Therefore, treatment will mirror your own personal residence (i.e. most expenses will be personal in nature and non-deductible).Any rent she does pay you is taxable in full with no deductions to offset.Then you contend with the gift tax issues.Generally not a good idea to rent to family, but if you do, make sure the rents are fair market. 

By any chance is anyone having any meets ups regularly that I can attend.