Help me make a 5 yr plan please!

[Max T.]

I have 10k in student loans.

I owe 155k on my 1st duplex (worth 250k)

I owe 160k on a SFR (worth 175k). This loan also covers the vacant lot next door, a buildable lot. New construction homes here sell around 350k.

I owe 92k on the SFH that I live in (worth 150k).

My full time gig is a high school teacher and wrestling coach.

I can save 1k per month. The home I live in still needs about 10k of renovations. The SFR doesn't generate much cash flow (150/month) due to the PMI. The duplex rents for a total of 2100/month, of which 1200 goes to the mortgage. The mortgage on the home I live in is 700. My student loan payments are 95/month.

Please help! I want to do a few things with my money but can't do them at the same time:

1. Pay off the student loans.

2. Finish the renovations on my home.

3. Pump money into a refinance of the SFR. Separate the lot from the house. Eliminate the PMI. Finance a new construction project on the lot to sell and keep the SFR.

4. Aggressively pay off the loan on my first duplex. When that mortgage is paid off it will generate excellent cash flow.

Options 3 and 4 are way more sexy. Option 2 is also high on my list because I live there with my wife and we did most of the work already. Option 1 is boring, but it's my only "bad debt!"

I'm expecting the community to push me on option 1. I could knock it out completely by summer, but that wouldn't leave me with much cash for option 2. I'll probably do both at the same time and take longer on both.

After 2 years of this options 1 and 2 should be finished. Then I could focus on options 3 or 4 (but which one gets priority?). After a few years of that, my DTI ratio should be back on track and I'll be tempted to buy again! Oh no! I really should get that house built and/or pay off the first duplex before adding to my portfolio, but it's so hard to pass up a good deal.

My goal is to make enough from my rental income to be able to retire from teaching. Obviously that means I should pay off that duplex as fast as possible... Please, tell me what I need to hear....

[Mark Ferguson]

How much do you owe on student loans? What is the rate? 

What is the rate on the duplex?  

If you pay off the loan on the duplex you are spending $155,000 in cash to chase down $1,200 a month. Not only will it take you years to pay it off, but what are you gaining once you pay it off? $14,400 a year on $155,000 is less than a ten percent a year return. You won't see that return for years until it is paid off.  It is not all about cash flow but cash on cash return. 

Will the SFR you are in now cash flow if you move out and rent it? You could continue the by a SFR owner occupant and rent in a year. repeat again.