After the sale of the company, we have:9-15 months of personal expenses in savings to live off ofStart with $100k cash and do micro flips to avoid the risk of a hard money lender and losing our tail if something doesn't go right or sell quick enoughOnce the house sells, reinvest all the cash back into the next flip and continue doing this until we are doing multiple flips at a time (he can manage 4 large projects at a time by himself, so we assume up to 4 active flips at a time eventually)Pros of doing this:No longer having to manage W2 employees/operations (this used to be my role but now that we have kids I want to stay home, not do this)Getting a larger chunk of cash to start flipping quicker vs waiting 1+ years to save enough cash for the first flipUsing cash reduces our risk of losing money with a hard money lender if the project takes longer to sell, rehab, etc.

Now, you can't do this with yourself, your business, and certain family members, due to the prohibited transaction rules governed by the tax code 4975. 2) Some individuals have large pre-tax 401ks that they rollover and then convert to the Roth IRA, paying the taxes now so they dont have to pay later out of the Roth. 

Note that he advises against putting large EMD down.

I have a CPA I work with who I’m sure will sort all of it out, just didn’t want to do something if it would cause a huge tax headache later.Do you know if you convert a STR to a LTR after a cost seg, will it cause a large repayment of taxes (I’m doing the cost segs to lower my W2 tax rate).

In my opinion investors buy properties with break even or negative cash flow and hope for large appreciation are taking a gamble.

Broker is out a very large amount of their upfront money .. scammers have borrowers info..

It is amazing what you can find in thrift stores and the like.Plus I put up a ton of large format photos fully framed.

I am wondering if it makes more sense to just deal with the large upfront cost to have the roof done fully or if repairing the damage will end up coming back to haunt me.It's a rather small house at just over 600sqft, for an addition is it really just a matter of getting estimates for the addition and comparing that to the additional rent I would get and seeing if it's worth it?

The large majority won't be worth it imo.

Looking for targeted courses on large multi-unit commercial/residential investing. 30-200 units.