Like many, money is an issue but I think I can put away 10-20K in the next ~2 years.Recommendations?

You’re going to have a legal local lease made up, research the local laws, make sure you don’t even appear to discriminate, figure how/where to advertise, do background checks and so on.

It sounds like you have a contract, but my guess is that it wasn't clear enough, and didn't cover some of the potential issues that could arise. 

In the past I have asked for a higher deposit but I just dont want to deal with any potential non payment issues nor evictions. 

Would I keep the deed in my name until it’s paid off or would it transfer to the buyers name and only revert if non payment is an issue?

@Ayyoub Reza in Michigan, if a lease is at least 12 months in length, you can charge tenants for maintenance and if not a health & safety issue, require them to fix it.Why would you have a lease end during the Oct-Feb timeframe, when it's the slowest time of the year for real estate sales & rentals?

Their expertise can help you make informed decisions.Insurance: Obtain appropriate insurance coverage for your properties to protect against risks such as property damage, liability, and loss of rental income.Legal Protection: Understand local laws and regulations governing real estate investments.

Some politicians are trying their best to head in that direction.As you know, In the US, laws are generally made state by state or even more locally.

I have been investing in Milwaukee since before it started trending 10 years ago and never had an issue with rental demand. 

I have State farms on my main house & attached ADU, but since they are NOT issuing new policies in California, I have been unable to find an INS company willing to just provide INS for my rental.