My plan was to try to manage most of it on my own first.

It would be best for you to reach out to an investor savvy CPA, there are over 20+ enlisted CPAs here in Biggerpockets assisting clients with their tax planning and strategies. 

I suggest you listen to free podcasts on land wholesaling, build a business plan, and then work it (Wholesaling Inc is a great one).  

Location is not an issue as most of them remotely assist RE clients with their tax planning and accounting. 

@Jacob Lopez, as others noted, house hacking is not really a cash flow play, in a traditional sense, since you are effectively removing 33-50% of the property from the rent roll.If you plan on living in a unit for a couple years, then holding longer as an investment, I would underwrite it as an investment.  

For estate planning purposes, we want to change the title to a revocable trust where my husband and I are the trustees. will this have a negative tax implication for 1031 purposes if we want to sell these and purchase properties prior to my husband's passing?

There's not necessarily a rush to reno immediately, just would definitely like to plan accordingly now so I am not completely caught off guard.

I stay away from contractors and rehab as I have zero knowledge in that department. 

When they sat down with my wife and I to show us the plans, they said they were hoping to give us 10K for the piece of property.I am hoping that someone has experience in this occuring and amount of money received.

I plan on doing more deals in the area and would love to add you to my network!