Usually a primary home is going to offer the best option to borrow against for higher LTV/CLTV, lower rate, and less fee's (No points).

Also, the home is located near the following: major freeway, hospitals and healthcare facilities, located within 15 mins of downtown, plenty of restaurant options nearby, etc.

I also value the planning element, especially if I’ll be setting up a trust, so now I feel torn about which option is best.EAs aren't going to focus on auditing and planning.

So my other options were to use my good credit but of course all of the loans want to use my personal credit and impact my debt-to-income.

If I owner occupied in b area or below I would consider this as an option.  

In fact, if your tenant does poorly, it may put you in a situation where selling is the best option and you will be stuck using the agent that caused the problem in the first place! 

I plan to hold this property towards retirement as it's in the area I grew up (obviously anything can change).I am receiving conflicting statements from contractors/friends/family on which roofing option to go with.

I've looked into a few options that won't cost 20%.

And no other buyers can get a loan on this thing either because there's no income to show.Anybody have any lending sources that might do this as a value add project?   

Many people that reach out don't have the 50% down to even achieve this option.