(we once paid $1800 to a big name plumber in town to replace 6in of plastic drainpipe under a stand alone tub). 3) We need better understanding of the legal structure (LLC) that we should have in place for our property, and also a tax advisor (CPA) to help with understanding deductions.

I'm known in my market as an investor-friendly Realtor, and people bring me deals based on this reputation.

Where have you successfully found reputable, investor-friendly lenders in the past?

I.e. if they get a tenant call for a clogged drain, they will call a plumber.  

They will still match you with CPAs with KNOWN poor reputations and a long history of client complaints/issues as happened with me. 

Disclaimer: I am not a professional plumber. 

My recomendation to you is to talk to a few reputable property management companies first, check the zip codes/ areas they work and then start your research from there. 

Many of the tax professionals on this forum are not "cheap" but can make a good fee for fixing situations where investors relied on poor advice from cheap advisors.My conclusion is to interview a few and go with a professional that you feel comfortable with no only their fee, but also their personality, their experience, their reputation, and their willingness to not only advise you as you start your journey but provide education and planning for what type of investor you want to be. 

With a HH, you learn how to analyze properties & markets, how to find an investor-friendly agent, how to spot value-add opportunities at properties, how to engage in a strong due diligence process, how to screen tenants, how to create a strong lease, how to manage the property, how to build a network of contractors, plumbers, electricians and other pros, how to manage the book keeping of the property, etc., etc., etc.

Plumbing all work, in 2023 we had to bypass some of the plumbing through the attic with PEX, plumber didn’t pull permit for this, so I have about 50% copper pipes behind the walls and 50% PEX in the attic.AC is from 2012, and water heater is from 2018.My fear comes from if anything weird would make the house completely uninsurable, I don’t mind paying a higher premium due to the roof being 14 years old or anything else, not sure how this is going to play out considering the insurance market in Florida.Thanks!