If the intent was always to flip the property, it shouldn't be taxed as long-term capital gain no matter when it's sold.

There are a bunch of good choices IMHO.We don't have leather but all our surfaces are super durable because they are higher end sofas and chairs.The 3 main couches are a pair of Basset and a La-Z-Boy.

The main way to reduce your DTI from RE is using a DSCR loan, however using an LLC is recommended to do so more effectively.

Ideally, I would love to buy a multi-family property and rent it out, I would consider house hacking but I mainly want to my first property to be one that I can improve on and have it generate income for me.

You get a great house to live in $150k-300k less than what you would otherwise pay for OR sell the main house as well for maximum profit.Photos are of a recent project from 2017.

the bathroom tile is too old", etc.I was the only person crawling under the house, going in the attic, looking in the Main panel.....everyone looked at me like I was nuts.So of course I bid it way higher than anyone else and did not get it.

Are you intentionally using all three just to pick up some of the services they each uniquely offer that don't overlap, and to be able to choose which ones are strong in a particular area?  

Several things to consider: 1) One of the main purposes of segmenting your assets into separate LLC's is so that your personal net worth or equity in other business ventures or properties isn't exposed, so unless you have a high net worth or a lot of equity in a property, it might not be worth bothering going the separate LLC route, especially when it restricts your financing of the property.  2) Most any commercial financing you get from a local bank for a small property is going to have recourse anyhow and require that you sign a personal guarantee, so you're still personally on the hook to the bank even in the case of a commercial loan.  3) If you're a newer investor and buying a deal that's tight on cash flow, or if you don't have a ton of cash sitting in the bank already, your greatest risk factor as an investor is your investment failing economically due to poor financing terms or not operating the investment properly, not because you get sued. 

Completely renovated main level:* Demoed and redid kitchen with new appliances* Refinished floors and reglazed bathroom* Replaced the roofComplete demoed and finished the basement and landscaping* Replaced half bath with full and added 2 bedrooms* Replaced entire plumbing including sewer line* Added second washer dryer* installed stamped concrete patio and walkway plus fence* All new landscapingWhat was the outcome?

It also makes it harder for other operators down the road--- not your main concern but we all impact each other.What about you and your wife live in the garage unit, and rent out the house for a lot more, at least until all this permitting is figured out.