The market is getting expensive and I’m worried it might be more difficult after I finally get current on my loan. 

What’s worse is that there is no consistency among the insurance companies.The ACORD forms and other Evidence of Insurance documents are notoriously cryptic and difficult to read.

Since you have 1099 income but no tax returns, traditional or FHA loans may be difficult to obtain.

But, compliance with securities laws are much more difficult.   

It is very difficult to vet an operator - they all say they are experienced, conservative and will be a good steward of your capital. 

It's very difficult to do that anymore today.Some people will call BS but I've found 9 times out of 10 those folks are doing their numbers wrong.

My biggest complaint for the most part now is that they don't seem to work that hard at finding new tenants, and they make it more difficult than it has to be for tenants to renew.

It is a business, so run it like one, as @Tom S. said, start the process and follow through.Unfortunately you're in a Blue state so this will be more difficult for you, so yes get a lawyer if they don't respond immediately to your 'pay or quit' notice.Don't take any more partial payments, that will delay your case!

It is all dependent on the numbers.If you are planning on putting low money down, the odds of it cash flowing (or even breaking even) in the first year would be difficult. 

For a problem that could have been resolved in a matter of hours/days or just a week at max, you can easily waste a few weeks here; - It is very often difficult to get them to act.