Has significant emotional upset with regards to this property and a series of previous contractors stealing money and doing poor work.Potential Total Profit at outset: $25,000 - anything I loan to investor 1's entity (after 10% sale & closing costs & concessions)4 weeks later / progress to date: I've spent/loaned $10,000 and worked 100 hours at the property to check items off what's needed before we can list the property on MLS.

What other items on here that require more labor dollars could I possibly knock out myself?

I do, however, pay extra for quality insurance policies that do not prorate needed repairs based on the age of the item getting repaired. 

Tell them what is needed, they'll tell you how it's done by the bid.For line items that are vastly different look at what makes up those differences?

This is the property in question: https://goo.gl/qjnBJK The top maintenance items are: cleaning up after tenants move out (paint, carpet cleaning), monthly landscaping ($90), and a smattering of appliance repairs.  

The contractor and I have a good relationship, he often does small work for me without a charge and in fact fixed some of the items the tenant had broke without a charge.

I would just take all the board classes and training after finding a company with training on capturing leads, keep your part time job for 6 months and then go full time, or start with rentals on the first months, works.

As part of this preparation, I am meeting with local CPAs to introduce myself and interview them for a potential fit for assisting me with tax related items.

See Ben Leybovich's article: https://www.biggerpockets.com/renewsblog/grant-cardone-primary-residence/As soon as I set roots in a particular city, I will probably purchase my primary home, regardless of price point, to take advantage of all the items you listed.

The seller should give you an inventory list of everything and in due diligence of the asset you verify everything.If at closing the Seller takes everything you have a legal claim since the items were identified in the executed PSA.