Does anyone know whether a bank would be open to doing a second mortgage if I purchased the property but did a subject to on the first mortgage?

The best thing you can do is find someone who you can talk with occasionally to help steer you for your first 1-2 deals.Look for someone local who does it by participating in local REI meetups, call a few real estate offices and ask for an agent who is also a RE investor, look online for a connection who can give you some time.RE is hyper-local so your best resource is someone who is familiar with the area you will be operating in.Even with 20 years experience I am glad to have a CFP who understands real estate so that I can bounce ideas around.

Here are some numbers185k PP = $1400 mortgage ARV=220Rents for 2500-3000 a month Saving 15%-20% for M&R, Cap Ex, VacancyIt will CASHFLOW very well...

Here's what I've been doing: I'm allocating 100% of the mortgage interest and half of the property tax as deductible.

However, it's crucial to differentiate between capital improvements, which can affect your tax situation and potential interest deductibility, and mere repairs or maintenance, which do not.Furthermore, the mortgage interest deduction is capped at interest on up to $750,000 of debt, a threshold that encompasses both your primary mortgage and any additional secured loans.

I pay $1000 per month on my own mortgage.

I’ve talked to a couple mortgage folks and haven’t gotten any great options yet. 

Looking to place the property at $495k and have about $240k left on the mortgage.

Tons of free information online on how to do this, what to look for in land, where to buy it and then resell it.

If house hacking doesn't pay the whole mortgage, that's ok, it's more important that your mindset is thinking as an investor and not a consumer.