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

This will allow you separate business income and expenses from personal income and expenses.Since you plan to house hack your bookkeeping and tax return preparation will be more complicated because a percentage of your home expenses will be personal deductions and some will be business deductions.

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.

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.

It also depends on the complexity of your flip and how your bookkeeping has been for expenses.

Basically, they name everyone because they’re hoping and counting on the fact that people set up their own LLCs and didn’t adhere to basic entity maintenance and kept things separate (like bookkeeping and separate bank accounts).

Hired part time admin assistant and 1/4 time services of book keeping professional. 

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. 

If our plan owned real property with many transactions, I would use a bookkeeper.

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.