This is not a big deal to deal with, but letting it slide is a gamble.

If i didn't have the prior inspection reports and the limited pictures they had available, it would be a major gamble even to come up with an offer price to begin with.

Our maintenance service is for your CONVENIENCE, it sure as hell isn't for ours, it's our #1 loss leader.

tenants in common is likely the cheapest route when purchasing property with another individual.However, creating an entity that will buy the property may be more convenient and provide some liability protection.Also, there may be some savings on fees / costs if your sister(who resides in California) is not a managing member / general partnership of the entity.The great thing about Florida is that they do not have a state income tax.Best of luck!

Is he testing you to see if you’ll take payments in dribs and drabs as he finds it convenient to pay?  

If you take cache via convenience check - there is fees upfront.I wouldn't take cash advances - rates are at the ball ark of default - like 18-24%....why?!?

When I left my corporate job, a colleague who was wiser than me at work told me that real estate is extremely risky and I am just gambling.

Hey,So my neighbor uses his house as a rental, he has another house he lives in down the street so it's convenient for him to keep an eye on it.

Should I find a way to cash out and get at least 200k invested back to reinvest (liquidity) or keep the convenience of a lower monthly payment when I refi?

In my opinion it's gambling and not investing.If you buy it and build on it or do something with it, then that's a different story.