When the housing market improves, the median home values increase. 

Consider whether you aim to build a substantial real estate portfolio for ongoing income or diversify investments over time.Risk Management: Assess risks associated with property ownership, including vacancies, maintenance costs, and market fluctuations.Risk Management: Assess risks such as vacancies, maintenance costs, and market fluctuations associated with owning multiple properties.Tax Planning: Work closely with a tax professional to develop a balanced strategy that maximizes current income offset with depreciation, while planning for depreciation recapture and optimizing use of 1031 exchanges.

Combined with the price I paid through the auction, they are much higher than market valueproperty 1: paid 100k, owe 170k.

I don't know your market, so I would not be able to advise you, but just consider the sellers motives and make the terms beneficial for both parties. 

To find a house where the seller is willing to sell it to you Sub2 the existing loan you need to do quite a bit of marketing.

Well, have a couple of competitors that are exclusively apartments/dev land for same.Their marketing is targeted at investors along with the mailing list.However, yes, you can get bad/good brokers in the same firm. 

Has everyone noticed that the rental market in PGH been especially difficult this year?

In market's like these, sometimes it's smart to stay cash heavy. 2.

Many wholesalers fail to understand the long-term value of maintaining strong relationships with buyers.

If you have a strong why and you are looking for the best avenue, that can be found.