I'm sorry you're having difficulty with your insurance company; however, when it comes to real estate investors, not all insurance is created equal. 

A mentor can guide you through the difficulties of real estate investment and provide insightful advice.To get practical experience, start with smaller, more manageable investments.

If I take HELOC to buy another property, then my current lender says "May face difficulty during your 2nd home purchase if DTI goes above 50% (1st mortgage + 2nd mortgage + HELOC + Other loans payment contributes to 43%)". 

I am sure building you into their team/portfolio would not be difficult. I

I am looking to buy a 3 family in fair haven and plan renting out each unit to section 8 tenants as they pay 1650 per unit... my question is how difficult is it to find section 8 tenants in this market?

If the price is right and you love the property, it is something to consider, but to me, the property would have to be super special and low-priced to justify that level of risk and potential difficulty in re-sale down the line.  

It is a simple process, 5 minutes to fill out the form, and 5 minutes at the county clerk.If you change it into an LLC you will probably have some difficulties getting a loan.

Price for tree removal is completely dependent on the difficulty of the removal.

Even if you just picked an average property, it should be worth at least 50% more than you paid, and the rent should be at least 50% more than it was when you bought it. one way to accelerate this concept is to find a property where the seller owns with no mortgage, and perhaps has difficulty selling because the property isn’t in good condition.  

The biggest difficulty owning property in Florida right now is the insurance.