Since you've already got a lot of the up-front expenses taken care of (e.g. furniture), you can always do my phase-in plan in reverse if necessary... start with them all as STRs, and if for whatever reason in the future you no longer want all 5 of them, you can gradually phase into LTRs (or mid-term stays like @Michael Nelson suggested).  

If they are quite a bit below market value, and pay on time every month, I would gradually increase the rent until it is at market value.

You will see overall a nice gradual increase with some downturns sprinkled in.

So the goal is to gradually increase rent at each tenant turnover.

If your annual adjusted income exceeds $100,000, the $25,000 loss deduction gradually phases out.

Our plan is to use his lines of credit for BRRR's, rehabs and other deals.I feel limited because of my credit situation, which is improving gradually, and all I really have to leverage is the equity in my rental.Our REI goals are parallel:  buy and hold, rehab and wholesale along the way.In a nutshell, he has money and sees value in investing in my city.  

We also hope to gradually get into buy and hold investment properties in the local area.I'm looking forward to learning a lot from what this great site has to offer - I'm already addicted to the podcasts!

However, I think you may be able to make a small profit if you don't have to hold it for too long (note that in Lake Mary, the stats show that the DOM has gradually increased over the last 3 months and with summer coming to an end, it may slow further - still healthy selling though) and get most of the work done by yourself.  

I bought my first property in 2017, 2nd property will be in 2018 and by 2019 I want to be buying 2-3 properties a year, gradually moving up in value and into multi-family.

To clarify, this is 102 multiunit properties transacted, not 51 duplexes for example. 2017 showed over twice the number of transactions as the 2011 low point and the trendline suggests that we will see a steady increase in 2018 units compared to 2017.Median sale price peaked in 2007 at 167k, and decreased gradually for the next 7 years before reversing itself back in the upward direction slowly.Volume is the total sum of transacted unit purchase prices. in 2005 nearly 54 million dollars in multifamily property was transacted, compared to just 33 million in 2017.