1031 Question and When to cash out

[Jake Rhodes]

All hypothetical - If I buy a flip and sell it for $150K, then use 1031 and buy another for $150K and flip for $200K, then on the third buy for $200K and flip for $250K.  At that point, Can I 1031 into a long term rental hold and miss having the tax penalty?  Or will it all catch up at that point and I will owe?  

Which amount will I be taxed on?  The $250K?  

If you have to use 1031 for the same value or greater, what happens when the price continues to escalate?  Do people try and get a larger multi-family at this point?

ANY other strategies?

Thanks in advance 

~Jake~