I stopped mailing and kept calling and what I am seeing is that there will be a 2-3 month delay on seller readiness off-market, but then there will be all the deals we want.

Trying to create a lease agreement at $2000 is not going to get you into a better position than just starting out by asking her to leave, and can just delay the eviction process by months if she ends up with a valid lease in hand.

If going the conventional several mortgages route, what are other safety measures to minimize risk besides a good insurance policy? 

Are you using cash for keys or any other methods for tenants with expired leases to prevent delays with holdover filings?

No 401k and IRA funds are just way easier to keep track of when invested in stocks, not to mention if you are doing RE properly you should have a minimal tax burden, so why would you use tax advantaged money to invest in it, assuming you want a diversified portfolio.

Tenant gave me a really delayed notice about his move out so this wasn't well planned out.Normally are permits required from City when parking a move out truck for an extended time?

However real estate investing it a totally new concept to me.I’ve read a few books and done quite of bit of research but I can’t decide if the strategy/method of investing I am thinking of would best work with my current situation.I do own a principle residence with a mortgage + heloc portion (currently have $30k in it with no balance) and minimal credit items on history and have over 800 score.

If you're looking for minimal upkeep and minimal reno - I'd probably avoid the central downtown area as you will need to make a heavy investment in those properties to get to that kind of cash flow or the high return you're looking for right away.Best of luck to you!!

For example, could $100k be used for delayed maintenance and the residual to pay down the mortgage?

I actually stumbled upon Alex a few days ago while reading articles about delayed financing.