Self managed HOAs are usually undercapitalized so you want to take a thorough review of the condition of the community to make sure there isn’t deferred maintenance because you might get hit with a special assessment if the board isn’t setting aside cash for those capital improvements.At face value, taking into consideration my typical financial objectives, I wouldn’t do this deal unless it was a much lower price.

I currently self manage so I don't have systems/team.

Than learn with that safety net until your ready to take things back over to self-manage again. 

I found the son on Facebook and sent a quick intro giving my condolences, expressed my interest in purchasing the property, and provided my phone # in case he decides to follow up.I'm in the process of preapproval with a couple lenders, and have reached out to a couple realtors in my area to see which may be a good fit.

Mostly MF and self storage.I bought an industrial property from a wholesaler, paid him a $600,000 fee. 

The following is not to express any level of happiness/unhappiness with build or process. 

Finding trademen and contractors is much tougher if you're self-managing.

Capacity and Tolerance. 1) Capacity: how many people can you comfortably fit in the property, is there room to add more, or add more value to the tenants to increase rent.2) Tolerance: How many people are you comfortable living with, if there are vacancies are you able to handle that.House hacking is an amazing path to homeownership, and a nice low barrier to entry into self managing your properties.

Next question.... will you self-manage it, or turn it over to a professional management company, or some type of hybrid? 

Personally, I self manage but have built systems to allow it to be fully remote and very passive.