From that meeting I've built good friendships with several people and we help each other regularly with mindset and holding each other accountable to our goals.

Any other gifts are pushing the line on friendship.

(Wait till you shoot yourself in the leg with a nail gun and you find out he never put you on his WC policy....friendship over.. lesson learned the hardway)

When you do that you put a value on that friendship and any good friendship should be invaluable.

You can be pushing friendships too far when you are holding your hand out, so even if it is offered, consider it a friendly offer more than a business relationship, I suggest making them offer at least three times before really considering them in a business dealing.....you can set the stage for the offers to be made, but don't just ask and never beg!!!

Through a connection at work I have stumbled upon an investment property that I want to purchase but since it is my first deal I want to make sure I am not missing something important.I developed a friendship with a colleague at work and he was gracious enough to take me around to see his rental properties. 

It's good you are asking for advice to learn from your mistakes,most of which were avoidable.You need to learn some of the rules of acquisition to prevent having problems in the the future.Rule of acquisition #3, "Never pay more for an acquisition than you have to".You paid way too much for a property in that bad a shape.If you can't get it for around 50% of the after repair value,let it go and find a better project.Rule of acquisition #21, "Never allow friendship to get in the way of profit".You can't make good business decisions if you are trying to keep a friendship from souring if you don't do what they want.You need to keep everything professional by only hiring employees you can terminate immediately when they fail to accomplish their tasks on time and on budget.Contractors are employees,not partners!

These aren't childhood friendships you are trying to maintain, this is a business dealing that requires legal remedy.

Can you request a friendship here and I will send a sample sheet for you.Thomas

I see all of these options as highly likely to ultimately end your friendship.