Hi Rene,It’s great that you’re planning to level up your bookkeeping!

With enough knowledge you can make a educated decision on which approach you take.My experience:I personally don't sign up for any program who take you aside during events and try to sell packages that is just blatant sales strategy.Once you sign up there is every attempt to make you sign for their programs for bookkeeping, registered agent, LLC or corp setup fee which have ridiculous even with platinum membership.Basic standard structure they suggest to take advantage of multiple deductions can be easily achieved by proper education or work with a good firm like https://wcginc.com  who is local to you.A umbrella C-crop to manage all other LLC properties and take advantage of many tax deductions that are not available with a llc, its also used to take losses up to 100K as startup expenses and dissolve the entity after few years.Few LLC entities for investing in Real Estate, etc preferably in Wyoming or Nevada ( you can find many companies online who can do this for $150 compared to anderson $1500-$3000) , they will claim they have a secret Operating agreement which is bogus.They certainly try to take advantage of tax loopholes and claim to be smart people, my view they are just taking advantage of numbers as per their own statements.

I’ve not used them (Stessa is working for me) but I’ve read positive things from others using those as a DIY book keeping solution.

This also helps with asset protection, monthly bookkeeping and annual tax return preparation. 

Realtor referred to the GC who was terrible at bookkeeping and communication.

Any time I have a client who did their bookkeeping for rental properties with QBO, it's it's always a lengthy process to try to sort it out. 

I use the lease feature from Rocket Lawyer as it's part of my tools stack from Baselane - my banking/bookkeeping/tenant management platform.

I am the only real estate investor with my bookkeeper and at first she thought this was a little overboard but once she started setting rules in Quickbooks to simplify her work she quickly realized how simple this method makes things.

We do all phases of the operation through. buy, rehab, rent, repairs, bookkeeping, tax preparation, etc.

LLCs can help streamline bookkeeping, but they don’t offer tax advantags unless structured as an S-Corp.