If you're willing to bend your timeline a little to give yourself the best shot at qualifying for 1031 exchanges and being super tax efficient with your properties, you could try doing the following: - Hold each successive property for at least 12 months before selling - make sure that you acquire property in one tax year and then don't sell that same property until the following tax yearI want to stress that you do not automatically lose out on 1031 treatment by not taking these steps, and similarly you don't automatically qualify for 1031 treatment by simply taking these steps. 

What would you call every single “highest and best” offer situation on the MLS other than an auction?

So, do operate within the BRRRR environment in an efficient way and not under such stress and pressure that means having enough money to front the contractor like 20% of the rehab. 

But you can still treat it as resulting in Ordinary Income even though it is reported on Schedule E, which lets you properly report in accordance with the tax results it seems you are shooting for under the tax return loophole.If your CPA is looking at switching it between schedules to get that tax result...it sounds like they don't understand the reporting position fully and/or they just don't know how to use their own software to address it.In summary, based on what you are describing for the situation, it should go on Schedule E, with what sounds like the resulting refund of $17k.

Hard to say right off the bat which is a better option since it depends a lot on what you are looking for and your situation but speaking with a lender that understands the application of primary residence loans in multifamily will be important to help you find the right option.

My family and I are planning to upgrade our living situation in a few years but we live in a HCOL (New York City) area so it’ll probably take that time to save up the down payment.

Sometimes a good person can just be in a situation, but they have the income to support the rent.  

If you try to evict on your own, there's a very good chance you'll just stretch it out and cost yourself some extra money and stress.

Creating these entities have costs especially the S-Corp so only do what works for your specific situation.

Hi there,Im new to the real estate game and I am faced with an interesting situation.