I plan to leave them enough that they can afford to buy a house or start a nest egg, but I am not leaving large sums to them.

Was planning on going to my first event next week.  

@John Brown Running a short-term rental (STR) on a subleased property, often called rental arbitrage, is feasible but requires careful planning.

. - Fortunately, our transparent systems allowed the owner to catch it:)- Full transparency - we would have never caught this honest mistake:(An owner also needs to be involved to approve & fund large expenses: maintenance, property tax & insurance payments (if they want to be more hands off), evictions, etc.A great PMC should also have a chat with you annually about your future plans for a property and your portfolio. 

You are procrastinating on the smallest of things which means you may lack the confidence to do what you are planning to do.

I can imagine it is considerably more work as well as I plan to manage myself.

Below are some actionable steps I plan to take after identifying a market:- find a rock star agent by referral and/or calling brokerages and asking to connect with their top producing agents- find a rock star contractor by referral and/or yelp- have control over construction by setting per diems to incentivize contractor to finish the project on time, within budget, and with good quality- leverage my rock star agent's time to check up on the construction process (checks and balances)- hire independent handymen/inspectors to check up on the construction process for a flat fee (checks and balances) There's competition everywhere, you won't escape that in any market. 

It seems like what you are planning would be in their best interests so I would discuss it with them first and then make that the impetus to sign a new lease and up the rent.

I always plan to have 6 months of holding costs available, for after I finish the flip, just in case I missed the market.If a lot of houses are sitting on the market for a long time, (can't sell) I'd definitely avoid it. 

I Know with my plan to acquire 5-10 properties in the next five years, at some point I am going to have to make 1-2 purchases a year.