How worried should I be about continuing to work with this property management company?

I will continue renting where I am currently (U-District) and rent my house (in whatever location it would be) .

2 - Is it common for the RE agent representing the buyer/seller to be anxious and annoying during this process when continuing to request extensions?

I have a little money saved up, and I'm going to continue doing so.

Do CODE VIOLATION SEARCH.9Calculate MAX Bid PriceOnce the properties are filtered with the above criteria, set the max bid price between 60% and 75% of Fair Market Value or ARV10Bid StrategyDetermine the low starting and maximum bidding amount, to be agreed by GENERAL PARTNERS11BiddingEnsure 5% of max bid price is in County bidding bank account 3 days prior to bidding12Property Win BidEnsure funds are wired to County bank within 24 hours of WIN13Send File to Lawyer/Title SearchIf property is still occupied, have Legal file a “Writ of Possession” to get former owner removed, Perform Extensive Title Review, Negotiate any existing Liens14Receive TitleReceipt of Certificate of Purchase, Certificate of Title to occur within 3-4 weeks from date of winning Bid, continue follow up with County until received

I have seen many stores going out of business and that technology has taken or will take physicality of having a store is losing  out over the Internet retail stores and I think that will continue. 

I'm looking to expand some more and continue to grow.

I am out of town and don't want to continue self-managing.

Or do I draw a hard line in the sand and point to the HOA rules drawn out in the Trust, Bylaws, and CC&R's and pursue legal action if he continues to refuse responsibility?

Continue doing it, until you get a girlfriend that is not ok with roommates.