LLC with S-corp election saves you the double taxation, you can put yourself on payroll as a W2.

Considering going in with other investors on a condotel unit in Las Vegas.Do condotels have anything different about them - as far as taxation/regulation/classification vs any other type of short term rental?

So you end up in the 5% and not in the 95%.Taxation of flipping has been discussed on literally hundreds of threads on this forum.

Which you will accomplish without any tap dancing.If you want to understand taxation of syndications in general, meaning outside the SDIRA accounts, read this:https://www.biggerpockets.com/forums/51/topics/839015-are-sy...

Keep growing that Roth IRA, as the principals of compounding interest in the absence of taxation are powerful! 

If you want tax-deductions now you might contribute to the pre-tax bucket and get a deductions, or if you want tax-free growth and tax-free distributions, you will look at contributing to Roth bucket, or maybe you do some to pre-tax and some to post tax Roth. 3) Simply put, Compounding Interest In the Absence of Taxation!

What would a taxation model look like in this scenario?

The repairs may be eligible for bonus depreciation.I recommend working with an accountant that specializes in real estate taxation. 

I recommend finding an accountant who specializes in real estate taxation and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

Regarding taxation, talk to your cpa on how insurance proceeds then the sale of a property after being damaged impacts your cost basis.So for me, spend the $ to demo the property and sell the land.