This is tough to do by the way because you cannot predict the market but you can make educated assumptions based on what you know.If long term, as long as the cash flow is great, there is no reason for you to be concerned about appreciation for now.

This agreement does not prevent you from making a passive investment in any publicly traded securities so long as such investment does not confer upon you or any entity that controls you, is controlled by you, or is under your common control of 5% or more of the outstanding securities of any such entity as described above.

@Adam H. you can't time the market, and if your time horizon is over the long term as long as you don't buy a bad property you'll still do alright.

But I think a refinance, and HELOC look to be a good fit, so long as the appraisal comes in high enough.

In my area, duplexes are rare  with a lot of competition for them, so buying a SFR and doing a garage conversion makes sense AS LONG as you are focused on cash flow and not trying to flip or leverage into the next property.

When I purchased my last duplex my pre qualification letter just stated something like "buyer can purchase property upto 170k" Would the bank be expecting me to have cash on hand for the amount of the 25% downpayment when refi'ing, or would they not be concerned about that as long as the property appraised 25% higher then what I owe my grandparents?

@Sherin SunnyAs long as they are smaller Multi-Fam you should be fine with a umbrella policy from your insurance provider.

Yes you can as long as you have a deposit and your lease states the deposit can be forefit for damage to the property. 

So long as I notate in my books what happened I doubt it would matter whether the transfer was started via check or digitally.

Can it be repeated and if so, identify how you will do so for the second and more importantly for scale in future.Not sure how you are affording your student debt payments but I have always gone with the notion that if I use leverage and create debt, so long as the money I am getting can be invested in an asset that produces a higher return, I have created arbitrage and could then pay down that debt with said arbitrage.