The way it sounds, someone conventional will come sooner than later.

The only thing that stopped me from buying my first rental sooner was my wife.

I’m simply saying I am going to work hard to try to make that sooner than later.

hell yes...... but you can also go bankrupt real fastIf its negative $400 cash flows now, the rent is going to have to go up a TON to truly cash flow positive once you factor ALL you expenses for CapX, maintenance etcExit strategy..... don't forget all you closing costs if you try and bail sooner rather than laterYou are making some BIG assumptions to rationalize this deal....that's a big red flag that unless you got deep pockets, this is not a deal for you

Without the address it is hard to say why the actual value is but here is a question to ask: if a home for example is worth say $85k with rents for example $850 per month but for the price you get a home with a great renovation, or you can buy the same house for say $65-$70k as it with some deferred repairs and majors only having half of their life left and slightly less on renovations: who would rather have it fully renovated at market value or get more equity but more repairs to come sooner than later? 

The sooner you start looking the sooner you will find one. 

After 12 months, possibly sooner, he is going to have $5k in profit from the refinance and a property cash flowing $270/month after property management fees are taken out.

Sooner or later, you will experience fear when you start taking new actions at new levels.

However if I go hard money, I can refi my existing property sooner, pull the cash in less than 30 days in time to cover the 25% for the 5th deal (the other 75% will be  a different PML).That said, should I wait to get approved on the conventional and risk losing this other deal or go hard money, get the 5th deal and deal with the higher interest on the hard money? 

Here is the ONLY way I would hold it...If you do not have any other good applicants that can take the unit sooner, I would take a non-refundable binder payment equal to one-month's rent NOW, then all of the move-in fees (first/last/security/pet fees) when you sign the lease for October 1st, which should be within a week.