The manager doesn't determine what they do and don't like, they 'manage' the HOA to comply with the law and guidance from the Board.

I honestly wouldn't trust anyone else with my clients but him when it comes to that local market.

Get your feet wet locally.

You can get that from your local S8 office.

depending on how backed up the county is it can e take a few months for court date. in essex county it took my mother in law about 8 months or so for the full process. she had an attorney, not sure if that sped anything up

Quote from @Gregory Schwartz: A local agent recently got sued for calling an old client who was on the Do Not Call list.

Would definitely check local zoning / code enforcement laws as well.  

There are a lot of good things about Wyoming LLCs, but the favorable Wyoming laws don't matter as much because the state you are in will apply the laws of the state the property is located in. 

I would consider the tenant's past, as well as the condition of the unit, my local market, and other factors.

If you are able to manage it yourself, I think you will get a lot of very helpful education in real estate by spending a least a year or two doing that.You'll be able to work with property managers a lot better if you've done the work yourself for a bit, and it also helps to get familiar with the various laws and regulations you have to comply with as the owner, even if you do have a property manager in place (e.g., the new RI rental registry and associated lead paint inspections/certificates).It's up to you whether you're able to do it, but I think you'll get a lot out of the experience if you can try it for a year or two.