I think the sum up is that people gave you feedback that you didnt want to hear or deal with, and your agent  enabled this because they didnt want to rock the boat. 

I would love to transition into real estate full-time, while also supplementing my income by doing freelance writing gigs online.

Regulations in Nevada, specifically the Las Vegas metro area, enable you to put a lot of the cost onto the tenant.

I would tell them it is what it is and they are welcome to supplement the air conditioner with portable A/C or window units.

So more so ideal for renovating the property and converting its use to business purposed.Someone also mentioned a reverse mortgage - a good idea if you don't go the STR route and instead want to supplement your father with income by tapping into that equity.

Many investors are looking for passive income, others would like to supplement a salary from a job or business they’re quite satisfied with; still others want an inflation hedge.So I ask, what goal(s) are you wanting to accomplish by utilizing real estate investing?

I've never really had an emergency that would have devastated me financially or put me in a very bad position.I think that I will take your advice and that of @Jeff Rabinowitz and make sure that I have a nice cash fund to supplement my credit lines!

I need the rental income to help supplement my income.

You will also need to identify local area vendors such as inspectors who are reputable to provide accurate information to enable you to make accurate determinations.

That is going to supplement the 529.