I had a taxable account, which I eventually just blew out on the secondary market to get the money back because the hassle was too high.I do still invest in a Roth IRA (takes out the hassle of taxes makes the returns manageable) and utilize it as the "bond component" in my Roth since bond prices have been in the toilet lately.

i.e. my W2 income plus the gain of the assets/buildings does not equal the "maximum taxable income" qualification of the rate chart. 

The financials are as follows:TSP(Government 401k):  approx $40kInherited IRA:  approx $115k (withdrawals affect taxable income levels)Cash:  approx $10k (recently paid off ALL consumer debt including car, so building this up at a rate of about $2.5k/mo)Precious metals:  probably about $20k worthReal Property: 4 houses#1: Single familyCurrent Mortgage: $163k (PITI = $970/mo)Estimated Value: $160kRent:  $1195/mo#2: Single FamilyCurrent Mortgage: approx $140k (PITI = $1088/mo)Estimated Value: $200kRent: $1385/mo#3: DuplexCurrent Mortgage:  approx $120k ($1120/mo)Estimated Value: $165kRent:  $825x2 ($1650/mo)#4: CondoCurrent Mortgage: $60k (PITI+HOA $853/mo)Estimated Value: $80kRent:  $850/mo  (I rent this one to my sister, so this one is a wash)So my questions are...

1. need to do STR at least for the rest of the year to qualify for bonus depreciation to reduce taxable w2 income, may later transfer to PMC and LTR with a long-term hold3. putting in around 30% (paying off seller equity), do have reserves for surprises, would want to refinance once rate drops to < 4.5 in few years (4-5) to take out equity and be able to hold the property at no to minimal cost.now this is all wish list and probably far from reality (day dreaming)

Can an s-corp owner /employee /officer claim an amount attributable to his own labor on a flip to help bring down the taxable profit?

My understanding was a loan against a 401k isn't a taxable event as opposed to cashing the 401k out.The idea was to get a larger loan with a potential longer repayment schedule from a local bank but it seems more complicated than I thought.

It's very possible that could be done without a taxable event as you have a capital account in the LLC and the property may offset the capital account. 

@Christian Manhard if I'm doing my math correctly it wouldn't help, because you'd pay yourself from the LLC thus reducing your taxable income by the same amount you increase it on the other end.

If I made a purchase and only broke even after 20 years, meaning that I never recorded any actual taxable income but the property is completely debt free after 20 years, is that a highly desireable situation? 

As I tell all wholesalers, remember that assigning an agreement of sale is a taxable event in Pennsylvania.