I've looked into wholesaling, which is an option, but I have basically no connections with buyers and I'd be nervous to start with no connections.

An option is an encumbrance, buy the property subject to the option at a lower price, if the optionee buys, you sell, if not, you still win.A deed in lieu of foreclosure can be had after the note is purchased at a discount.You can buy the note at a discount and have the owner refinance, same with installment contracts. 

Another option is to go to investor groups in your area (investor conferences, seminars, etc.). 

Upon retirement, I have the option to allocate a significant portion of my income to pay off all four properties.My inquiry arises from an opportunity that recently presented itself: the chance to invest in new duplexes in Indiana.

I've been in REI a long time and have seen the good, the bad, and the ugly, but $60k of damage from one tenant indicates gross negligence on the part of the property manager.I'd suggest three things: 1) Study the contract you have with the PM company, and talk with your attorney ASAP to see whether a lawsuit is feasible/advisable, 2) Get at least three bids from other contractors on the repairs (and before you hire any contractors, study up thoroughly on how to properly vet and manage contractors--there's plenty of info about this on BP) 3) Don't do any more business with the PM company (or any contractors they refer), and keep them at arm's length while you discuss your legal options with your attorney.

Posting on a local RE group in that area might be a good option as well to get recommendations from others

Hey Lucas, another option instead of creative financing is a DSCR loan for an investment property.

Hard work and sacrifice will work as a magnet for people to help you because they see you going through what they went throughFor financing options I like the BP book "investing with no or low money down" but this isn't possible unless you get a really good off market deal.

We recevied a proposal from a billboard company to build a full sized billboard. the research has been conducted and a written lease has been written and presented to us for 1k/mo, 20 years + 20 yr option, with 10% rate increases every 5 yrs.

I've never paid to have a metal roof installed so don't know labor charges (I've always done my own)You're right about the longevity – metal roofs can last a very long time, making them a cost-effective option in the long run.