Am I getting something less with the cheaper companies?

If you do pull any funds out - it would be considered a distribution, which is a taxable event and if this happens before retirement age penalties would also apply.In addition that that, flipping activity may be considered an active business, and profit might be subject to Unrelated Business Income Tax. 

Rent is cheaper 65% then section 8 program (smaller payout)I prefer to put the property on section 8 because i KNOW that i will receive my money, or at least most of it.

It is much cheaper and I would certainly prefer to pay my friends and family before a HML. 

An individual generally must include any pretax assets that are converted to Roth IRAs in taxable income, but the 10 percent early distribution penalty tax does not apply.Any basis in the Traditional IRA (e.g., nondeductible IRA contributions, retirement plan rollovers of after-tax assets) is not taxable when converted.Tax laws require individuals to treat all of their Traditional and SIMPLE IRAs as one IRA when figuring the taxation of their conversions.

sounds like you should lower the rent. depending on what you're asking, i'd drop it 8-10%.... still cheaper than a month's vacancy.

I'm thinking of more permanent structures like cabins rather than the tumbleweed model (which I don't really understand because RV's are cheaper per square foot and have some great features that Tiny Houses don't have like slide outs). but the strategy is the same.I'd love to hear your thoughts.

It's very frustrating spending a ton of time and sharing experience only for someone to give it to their brother-in-law who's out of work and will do it cheaper.

Just to add to Wayne's comment.Over the four year holding period, the depreciation you took reduced your taxable rental income by $10K.  

If data was cheaper to come by in this industry, a lot could be done with it.If you're familiar with Python, this GitHub may be useful.