For example property managers often keep a list of contractors that they hire to maintain their properties. 

Now that I'm unable to maintain it I'm thinking of selling an buying 2 condos north and south 1 primarily for living and one for 2nd home  I know 2/3 is going to be capital gains and some getting to be written off for work done, what would be my best route to attack my problem Bite the bullet and pay the capital gains / really don’t want to go 1031 because I think I’ll be back in the same position 

It’s been a really good learning experience if anything.As I see it these are my options:-Leave the first two properties alone, continue saving, and purchase once I have enough saved up-Refinance out of the first property back to a 30 year mortgage with considerations on maintaining a positive cash flow and use that money as part of the down payment -Sell the first property outright and do a 1031 exchange.Pros: Get out of a new property before needed repairs, get rid of a property that doesn’t perform that great by rental standardsCons: Lose low financing, lose good tenantsAre there other options I'm not considering? 

Much of the complexity and billing in your situation would be dependent on how good your record keeping is - perhaps touch base with your chosen accountant on a good system to maintain everything.

The utilities and roads are maintained by the city.  

In fact you may end up finding that they cost you more to keep maintained and rented. 

They’ll probably do a pretty poor job, or won’t maintain anything they “improve” and you’ll have to change it when they leave anyways.

You have two attorneys, need to maintain 2 relationships. 

@Samuel IwuThe same theory is maintained regardless of the situation- even with the rehab property.

BTW, as the owner leasing the property, I am required by law to maintain the property to a habitable condition no matter what might be in the option about the tenant doing the work.If I am selling on a land contract, only in certain states can you do this, then the title transfers when the conditions of the land contract are satisfied.If I am selling and agree to carry back a note, the title will transfer at the close of escrow, the new owner is just that, the owner of the title and my interest moves from being an owner to being the lender with a lien on the property.